ACS Publications. Most Trusted. Most Cited. Most Read
My Activity
CONTENT TYPES

Figure 1Loading Img

Palladium-Catalyzed Asymmetric Addition of Pronucleophiles to Allenes

View Author Information
Department of Chemistry, Stanford University, Stanford, California 94305-5080
Cite this: J. Am. Chem. Soc. 2003, 125, 15, 4438–4439
Publication Date (Web):March 25, 2003
https://doi.org/10.1021/ja029190z
Copyright © 2003 American Chemical Society

    Article Views

    4168

    Altmetric

    -

    Citations

    LEARN ABOUT THESE METRICS
    Read OnlinePDF (39 KB)
    Supporting Info (2)»

    Abstract

    Abstract Image

    Simple additions are the most atom economic way to effect alkylations. The ability to effect the hydrocarbonation of allenes asymmetrically then becomes a highly efficient alkylation protocol. The first example of such a protocol involves the ability of a palladium(0) catalyst derived from palladium trifluoroacetate dimer and the bis-2-diphenylphosphinobenzamide of trans-1,2-diamininocyclohexane to catalyze additions to benzyloxyalkene. Various substituted Meldrum's acids including hydroxy Meldrum's acid react well in the presence of 1 mol % trifluoroacetic acid to give one regioisomer with ee's ranging from 82 to 99%. Switching to azlactones to access unusual quarternary amino acids requires somewhat more basic conditions. Thus, use of 2 mol % potassium α-butoxide and 20 mol % hippuric acid leads to a smooth reaction to produce a simple regiosomer. This nucleophile raises the question of facial selectivity with respect to both the nucleophile and the electrophile. Excellent diastereoselectivity (dr 13−20:1) and enantioselectivity (85−94% ee) are obtained. Thus, a new approach for asymmetric allylic alkylations of carbon pronucleophiles by simple additions provides a very efficient, more atom economic strategy for asymmetric C−C bond formation.

    *

    In papers with more than one author, the asterisk indicates the name of the author to whom inquiries about the paper should be addressed.

    Supporting Information Available

    ARTICLE SECTIONS
    Jump To

    Spectroscopic and analytical data for 5af and 8ae and representative procedures for the synthesis of 5a and 8a (PDF). This material is available free of charge via the Internet at http://pubs.acs.org.

    Terms & Conditions

    Most electronic Supporting Information files are available without a subscription to ACS Web Editions. Such files may be downloaded by article for research use (if there is a public use license linked to the relevant article, that license may permit other uses). Permission may be obtained from ACS for other uses through requests via the RightsLink permission system: http://pubs.acs.org/page/copyright/permissions.html.

    Cited By

    This article is cited by 186 publications.

    1. Miguel Yus, Carmen Nájera, Francisco Foubelo, José M. Sansano. Metal-Catalyzed Enantioconvergent Transformations. Chemical Reviews 2023, 123 (20) , 11817-11893. https://doi.org/10.1021/acs.chemrev.3c00059
    2. Chunming Gui, Yuanyuan Peng, Yang Zhou, Yixuan Zheng, Haifeng Wang, Qiongjiao Yan, Hui Zhou, Wei Wang, Fen-Er Chen. Cu-Catalyzed Intermolecular Asymmetric Propargylic Substitution of N-Hydroxyphthalimide Esters with Propargyl Carbonates. ACS Catalysis 2023, 13 (20) , 13735-13742. https://doi.org/10.1021/acscatal.3c03814
    3. Sheng-Suo Zhou, Xing-Yun Sun, Wen-Kai Liu, Jia-Yu Song, Zheng Wang, Zheng-Hang Qi, Xing-Wang Wang. COAP-Pd Catalyzed Asymmetric Allylic Alkylation of Azlactones with MBH Carbonates: Access to Unnatural α-Quaternary Stereogenic Glutamic Acid Derivatives. The Journal of Organic Chemistry 2023, 88 (16) , 11867-11873. https://doi.org/10.1021/acs.joc.3c01152
    4. Shao-Qian Yang, Ai-Jun Han, Yang Liu, Xin-Yuan Tang, Guo-Qiang Lin, Zhi-Tao He. Catalytic Asymmetric Hydroalkoxylation and Formal Hydration and Hydroaminoxylation of Conjugated Dienes. Journal of the American Chemical Society 2023, 145 (7) , 3915-3925. https://doi.org/10.1021/jacs.2c11843
    5. Ke-Qin Wu, Hui Li, Ao Zhou, Wei-Ran Yang, Qin Yin. Palladium-Catalyzed Chemo- and Regioselective C–H Bond Functionalization of Phenols with 1,3-Dienes. The Journal of Organic Chemistry 2023, 88 (4) , 2599-2604. https://doi.org/10.1021/acs.joc.2c02697
    6. Takahiro Sawano, Masaki Ono, Ami Iwasa, Masaya Hayase, Juri Funatsuki, Ayumu Sugiyama, Eri Ishikawa, Takeshi Yoshikawa, Ken Sakata, Ryo Takeuchi. Iridium-Catalyzed Branch-Selective Hydroalkylation of Simple Alkenes with Malonic Amides and Malonic Esters. The Journal of Organic Chemistry 2023, 88 (3) , 1545-1559. https://doi.org/10.1021/acs.joc.2c02599
    7. Jie Zhang, Yaning Wang, Chang You, Mingying Shi, Xueling Mi, Sanzhong Luo. Asymmetric Coupling of β-Ketocarbonyls and Alkynes by Chiral Primary Amine/Rh Synergistic Catalysis. Organic Letters 2022, 24 (5) , 1186-1189. https://doi.org/10.1021/acs.orglett.1c04334
    8. Hongfa Wang, Ruiyuan Zhang, Qinglong Zhang, Weiwei Zi. Synergistic Pd/Amine-Catalyzed Stereodivergent Hydroalkylation of 1,3-Dienes with Aldehydes: Reaction Development, Mechanism, and Stereochemical Origins. Journal of the American Chemical Society 2021, 143 (29) , 10948-10962. https://doi.org/10.1021/jacs.1c02220
    9. Geonhui Park, Christopher W. Bielawski. Ring Opening Metathesis Polymerization of Cyclic Allenes. Macromolecules 2021, 54 (13) , 6135-6143. https://doi.org/10.1021/acs.macromol.1c00571
    10. Hongfang Li, Ijaz Khan, Meiqi Li, Zheng Wang, Xue Wu, Kuiling Ding, Yong Jian Zhang. Pd-Catalyzed Regio- and Enantioselective Aminoarylation of Allenols with Aryl Iodides and 2-Pyridones. Organic Letters 2021, 23 (9) , 3567-3572. https://doi.org/10.1021/acs.orglett.1c00959
    11. Jun Zheng, Ali Nikbakht, Bernhard Breit. Dual Palladium/Photoredox-Catalyzed Enantioselective and Regioselective Decarboxylative Hydroaminoalkylation of Allenes. ACS Catalysis 2021, 11 (6) , 3343-3350. https://doi.org/10.1021/acscatal.1c00153
    12. Rémi Blieck, Marc Taillefer, Florian Monnier. Metal-Catalyzed Intermolecular Hydrofunctionalization of Allenes: Easy Access to Allylic Structures via the Selective Formation of C–N, C–C, and C–O Bonds. Chemical Reviews 2020, 120 (24) , 13545-13598. https://doi.org/10.1021/acs.chemrev.0c00803
    13. Nicholas J. Galan, Johnathan N. Brantley. General Access to Allene-Containing Polymers Using the Skattebøl Rearrangement. ACS Macro Letters 2020, 9 (11) , 1662-1666. https://doi.org/10.1021/acsmacrolett.0c00745
    14. Qinglong Zhang, Dongfang Dong, Weiwei Zi. Palladium-Catalyzed Regio- and Enantioselective Hydrosulfonylation of 1,3-Dienes with Sulfinic Acids: Scope, Mechanism, and Origin of Selectivity. Journal of the American Chemical Society 2020, 142 (37) , 15860-15869. https://doi.org/10.1021/jacs.0c05976
    15. Takahiro Sawano, Kei Ogihara, Jun Sagawa, Masaki Ono, Ryo Takeuchi. Iridium-Catalyzed Hydroalkylation of Aliphatic Alkenes with β-Ketoesters: Formal Hydroalkylation with Methyl Ketones. Organic Letters 2020, 22 (15) , 6187-6191. https://doi.org/10.1021/acs.orglett.0c02291
    16. Jinjin Hu, Shulei Pan, Shuai Zhu, Peiyuan Yu, Ruigang Xu, Guofu Zhong, Xiaofei Zeng. Pd-Catalyzed Dearomative Asymmetric Allylic Alkylation of Naphthols with Alkoxyallenes. The Journal of Organic Chemistry 2020, 85 (12) , 7896-7904. https://doi.org/10.1021/acs.joc.0c00582
    17. Chibueze I. Onyeagusi, Xinxin Shao, Steven J. Malcolmson. Enantio- and Diastereoselective Synthesis of Homoallylic α-Trifluoromethyl Amines by Catalytic Hydroalkylation of Dienes. Organic Letters 2020, 22 (4) , 1681-1685. https://doi.org/10.1021/acs.orglett.0c00342
    18. Zongpeng Zhang, Fan Xiao, Hui-Min Wu, Xiu-Qin Dong, Chun-Jiang Wang. Pd-Catalyzed Asymmetric Hydroalkylation of 1,3-Dienes: Access to Unnatural α-Amino Acid Derivatives Containing Vicinal Quaternary and Tertiary Stereogenic Centers. Organic Letters 2020, 22 (2) , 569-574. https://doi.org/10.1021/acs.orglett.9b04341
    19. Nathan J. Adamson, Steven J. Malcolmson. Catalytic Enantio- and Regioselective Addition of Nucleophiles in the Intermolecular Hydrofunctionalization of 1,3-Dienes. ACS Catalysis 2020, 10 (2) , 1060-1076. https://doi.org/10.1021/acscatal.9b04712
    20. Qinglong Zhang, Huimin Yu, Lulu Shen, Tianhua Tang, Dongfang Dong, Weiwei Chai, Weiwei Zi. Stereodivergent Coupling of 1,3-Dienes with Aldimine Esters Enabled by Synergistic Pd and Cu Catalysis. Journal of the American Chemical Society 2019, 141 (37) , 14554-14559. https://doi.org/10.1021/jacs.9b07600
    21. Tian-Ci Wang, Lian-Feng Fan, Yang Shen, Pu-Sheng Wang, Liu-Zhu Gong. Asymmetric Allylic C–H Alkylation of Allyl Ethers with 2-Acylimidazoles. Journal of the American Chemical Society 2019, 141 (27) , 10616-10620. https://doi.org/10.1021/jacs.9b05247
    22. Hua-Chen Lin, Pei-Pei Xie, Zhen-Yao Dai, Shuo-Qing Zhang, Pu-Sheng Wang, Yu-Gen Chen, Tian-Ci Wang, Xin Hong, Liu-Zhu Gong. Nucleophile-Dependent Z/E- and Regioselectivity in the Palladium-Catalyzed Asymmetric Allylic C–H Alkylation of 1,4-Dienes. Journal of the American Chemical Society 2019, 141 (14) , 5824-5834. https://doi.org/10.1021/jacs.8b13582
    23. Lei Cheng, Ming-Ming Li, Li-Jun Xiao, Jian-Hua Xie, Qi-Lin Zhou. Nickel(0)-Catalyzed Hydroalkylation of 1,3-Dienes with Simple Ketones. Journal of the American Chemical Society 2018, 140 (37) , 11627-11630. https://doi.org/10.1021/jacs.8b09346
    24. Rémi Blieck, Racha Abed Ali Abdine, Marc Taillefer, Florian Monnier. Regio- and Stereoselective Copper-Catalyzed Allylation of 1,3-Dicarbonyl Compounds with Terminal Allenes. Organic Letters 2018, 20 (8) , 2232-2235. https://doi.org/10.1021/acs.orglett.8b00575
    25. Nathan J. Adamson, Katherine C. E. Wilbur, and Steven J. Malcolmson . Enantioselective Intermolecular Pd-Catalyzed Hydroalkylation of Acyclic 1,3-Dienes with Activated Pronucleophiles. Journal of the American Chemical Society 2018, 140 (8) , 2761-2764. https://doi.org/10.1021/jacs.7b13300
    26. Wenfang Xiong, Donghao Yan, Chaorong Qi, and Huanfeng Jiang . Palladium-Catalyzed Four-Component Cascade Reaction for the Synthesis of Highly Functionalized Acyclic O,O-Acetals. Organic Letters 2018, 20 (3) , 672-675. https://doi.org/10.1021/acs.orglett.7b03808
    27. Zi Liu and Bernhard Breit . Rhodium-Catalyzed Regio- and Enantioselective Addition of N-Hydroxyphthalimide to Allenes: A Strategy To Synthesize Chiral Allylic Alcohols. Organic Letters 2018, 20 (1) , 300-303. https://doi.org/10.1021/acs.orglett.7b03709
    28. Ivan Bernar, Béla Fiser, Daniel Blanco-Ania, Enrique Gómez-Bengoa, and Floris P. J. T. Rutjes . Pd-Catalyzed Hydroamination of Alkoxyallenes with Azole Heterocycles: Examples and Mechanistic Proposal. Organic Letters 2017, 19 (16) , 4211-4214. https://doi.org/10.1021/acs.orglett.7b01826
    29. Wei-Feng Zheng, Qiu-Jing Xu, and Qiang Kang . Rhodium/Lewis Acid Catalyzed Regioselective Addition of 1,3-Dicarbonyl Compounds to Internal Alkynes. Organometallics 2017, 36 (12) , 2323-2330. https://doi.org/10.1021/acs.organomet.7b00284
    30. Jie Zhu, Mao Mao, Huan-Jing Ji, Jiang-Yan Xu, and Lei Wu . Palladium-Catalyzed Cleavage of α-Allenylic Aryl Ether toward Pyrazolemethylene-Substituted Phosphinyl Allenes and Their Transformations via Alkenyl C–P(O) Cleavage. Organic Letters 2017, 19 (8) , 1946-1949. https://doi.org/10.1021/acs.orglett.7b00213
    31. Han Zhou, Yaning Wang, Long Zhang, Mao Cai, and Sanzhong Luo . Enantioselective Terminal Addition to Allenes by Dual Chiral Primary Amine/Palladium Catalysis. Journal of the American Chemical Society 2017, 139 (10) , 3631-3634. https://doi.org/10.1021/jacs.7b00437
    32. Matthew J. Goldfogel, Courtney C. Roberts, Rajith S. Manan, and Simon J. Meek . Diastereoselective Synthesis of γ-Substituted 2-Butenolides via (CDC)-Rh-Catalyzed Intermolecular Hydroalkylation of Dienes with Silyloxyfurans. Organic Letters 2017, 19 (1) , 90-93. https://doi.org/10.1021/acs.orglett.6b03369
    33. Kin S. Yang, John A. Gurak, Jr., Zhen Liu, and Keary M. Engle . Catalytic, Regioselective Hydrocarbofunctionalization of Unactivated Alkenes with Diverse C–H Nucleophiles. Journal of the American Chemical Society 2016, 138 (44) , 14705-14712. https://doi.org/10.1021/jacs.6b08850
    34. Tianli Wang, Zhaoyuan Yu, Ding Long Hoon, Claire Yan Phee, Yu Lan, and Yixin Lu . Regiodivergent Enantioselective γ-Additions of Oxazolones to 2,3-Butadienoates Catalyzed by Phosphines: Synthesis of α,α-Disubstituted α-Amino Acids and N,O-Acetal Derivatives. Journal of the American Chemical Society 2016, 138 (1) , 265-271. https://doi.org/10.1021/jacs.5b10524
    35. Thorsten M. Beck and Bernhard Breit . Regioselective Rhodium-Catalyzed Addition of 1,3-Dicarbonyl Compounds to Terminal Alkynes. Organic Letters 2016, 18 (1) , 124-127. https://doi.org/10.1021/acs.orglett.5b03391
    36. Jiawang Liu, Zhaobin Han, Xiaoming Wang, Zheng Wang, and Kuiling Ding . Highly Regio- and Enantioselective Alkoxycarbonylative Amination of Terminal Allenes Catalyzed by a Spiroketal-Based Diphosphine/Pd(II) Complex. Journal of the American Chemical Society 2015, 137 (49) , 15346-15349. https://doi.org/10.1021/jacs.5b07764
    37. Liyin Jiang, Tao Jia, Min Wang, Jian Liao, and Peng Cao . Pd-Catalyzed Enantioselective Hydroalkoxylation of Alkoxyallenes with Phenol for Construction of Acyclic O,O-Acetals. Organic Letters 2015, 17 (5) , 1070-1073. https://doi.org/10.1021/acs.orglett.5b00146
    38. Philipp Koschker, Matthias Kähny, and Bernhard Breit . Enantioselective Redox-Neutral Rh-Catalyzed Coupling of Terminal Alkynes with Carboxylic Acids Toward Branched Allylic Esters. Journal of the American Chemical Society 2015, 137 (8) , 3131-3137. https://doi.org/10.1021/jacs.5b01131
    39. Barry M. Trost, Etienne J. Donckele, David A. Thaisrivongs, Maksim Osipov, and James T. Masters . A New Class of Non-C2-Symmetric Ligands for Oxidative and Redox-Neutral Palladium-Catalyzed Asymmetric Allylic Alkylations of 1,3-Diketones. Journal of the American Chemical Society 2015, 137 (7) , 2776-2784. https://doi.org/10.1021/jacs.5b00786
    40. Yao-Zhong Chen, Ling Zhang, Ai-Min Lu, Fang Yang, and Lei Wu . α-Allenyl Ethers as Starting Materials for Palladium Catalyzed Suzuki–Miyaura Couplings of Allenylphosphine Oxides with Arylboronic Acids. The Journal of Organic Chemistry 2015, 80 (1) , 673-680. https://doi.org/10.1021/jo502485u
    41. Kun Xu, Vahid Khakyzadeh, Timm Bury, and Bernhard Breit . Direct Transformation of Terminal Alkynes to Branched Allylic Sulfones. Journal of the American Chemical Society 2014, 136 (46) , 16124-16127. https://doi.org/10.1021/ja509383r
    42. Wontaeck Lim, Jungjoon Kim, and Young Ho Rhee . Pd-Catalyzed Asymmetric Intermolecular Hydroalkoxylation of Allene: An Entry to Cyclic Acetals with Activating Group-Free and Flexible Anomeric Control. Journal of the American Chemical Society 2014, 136 (39) , 13618-13621. https://doi.org/10.1021/ja508587f
    43. Valerian Gobé and Xavier Guinchard . Pd(0)-Catalyzed Tandem Deprotection/Cyclization of Tetrahydro-β-carbolines on Allenes: Application to the Synthesis of Indolo[2,3-a]quinolizidines. Organic Letters 2014, 16 (7) , 1924-1927. https://doi.org/10.1021/ol500448j
    44. Juan Marco-Martínez, Silvia Reboredo, Marta Izquierdo, Vanesa Marcos, Juan Luis López, Salvatore Filippone, and Nazario Martín . Enantioselective Cycloaddition of Münchnones onto [60]Fullerene: Organocatalysis versus Metal Catalysis. Journal of the American Chemical Society 2014, 136 (7) , 2897-2904. https://doi.org/10.1021/ja500071k
    45. Changkun Li and Bernhard Breit . Rhodium-Catalyzed Chemo- and Regioselective Decarboxylative Addition of β-Ketoacids to Allenes: Efficient Construction of Tertiary and Quaternary Carbon Centers. Journal of the American Chemical Society 2014, 136 (3) , 862-865. https://doi.org/10.1021/ja411397g
    46. Lindsay M. Repka and Sarah E. Reisman . Recent Developments in the Catalytic, Asymmetric Construction of Pyrroloindolines Bearing All-Carbon Quaternary Stereocenters. The Journal of Organic Chemistry 2013, 78 (24) , 12314-12320. https://doi.org/10.1021/jo4017953
    47. Meiling Li, Swarup Datta, David M. Barber, and Darren J. Dixon . Dual Amine and Palladium Catalysis in Diastereo- and Enantioselective Allene Carbocyclization Reactions. Organic Letters 2012, 14 (24) , 6350-6353. https://doi.org/10.1021/ol303128s
    48. Shi-Hui Shi, Fu-Ping Huang, Ping Zhu, Zhen-Wen Dong, and Xin-Ping Hui . Synergistic Chiral Ion Pair Catalysts for Asymmetric Catalytic Synthesis of Quaternary α,β-Diamino Acids. Organic Letters 2012, 14 (8) , 2010-2013. https://doi.org/10.1021/ol300510b
    49. Barry M. Trost and Lara C. Czabaniuk . Benzylic Phosphates as Electrophiles in the Palladium-Catalyzed Asymmetric Benzylation of Azlactones. Journal of the American Chemical Society 2012, 134 (13) , 5778-5781. https://doi.org/10.1021/ja301461p
    50. Philipp Koschker, Alexandre Lumbroso, and Bernhard Breit . Enantioselective Synthesis of Branched Allylic Esters via Rhodium-Catalyzed Coupling of Allenes with Carboxylic Acids. Journal of the American Chemical Society 2011, 133 (51) , 20746-20749. https://doi.org/10.1021/ja210149g
    51. Barry M. Trost, Jia Xie, and Joshua D. Sieber . The Palladium Catalyzed Asymmetric Addition of Oxindoles and Allenes: An Atom-Economical Versatile Method for the Construction of Chiral Indole Alkaloids. Journal of the American Chemical Society 2011, 133 (50) , 20611-20622. https://doi.org/10.1021/ja209244m
    52. Asa D. Melhado, Giovanni W. Amarante, Z. Jane Wang, Marco Luparia, and F. Dean Toste . Gold(I)-Catalyzed Diastereo- and Enantioselective 1,3-Dipolar Cycloaddition and Mannich Reactions of Azlactones. Journal of the American Chemical Society 2011, 133 (10) , 3517-3527. https://doi.org/10.1021/ja1095045
    53. Manuel Weber, Sascha Jautze, Wolfgang Frey and René Peters. Bispalladacycle-Catalyzed Brønsted Acid/Base-Promoted Asymmetric Tandem Azlactone Formation−Michael Addition. Journal of the American Chemical Society 2010, 132 (35) , 12222-12225. https://doi.org/10.1021/ja106088v
    54. Xiaodong Liu, Leijiao Deng, Xianxing Jiang, Wenjin Yan, Chunliang Liu and Rui Wang. Asymmetric Aza-Mannich Addition of Oxazolones to N-Tosyl Aldimines: Synthesis of Chiral α-Disubstituted α,β-Diamino Acids. Organic Letters 2010, 12 (4) , 876-879. https://doi.org/10.1021/ol902916s
    55. Gen Onodera, Minoru Kato, Ryo Kawano, Yuri Kometani and Ryo Takeuchi. Highly Regio- and Stereoselective Addition of 1,3-Diketones to Internal Alkynes Catalyzed by Cationic Iridium Complex. Organic Letters 2009, 11 (21) , 5038-5041. https://doi.org/10.1021/ol9020095
    56. Xiao-Qing Zhu, Hao Liang, Yan Zhu and Jin-Pei Cheng. Hydride Affinities of Cumulated, Isolated, and Conjugated Dienes in Acetonitrile. The Journal of Organic Chemistry 2008, 73 (21) , 8403-8410. https://doi.org/10.1021/jo801536m
    57. Zhi-Feng Lu, Yong-Miao Shen, Jia-Jun Yue, Hong-Wen Hu and Jian-Hua Xu. Photoinduced Three-Component Reactions of Tetracyanobenzene with Alkenes in the Presence of 1,3-Dicarbonyl Compounds as Nucleophiles. The Journal of Organic Chemistry 2008, 73 (20) , 8010-8015. https://doi.org/10.1021/jo801448v
    58. Silvia Cabrera, Efraim Reyes, José Alemán, Andrea Milelli, Sara Kobbelgaard and Karl Anker Jørgensen. Organocatalytic Asymmetric Synthesis of α,α-Disubstituted α-Amino Acids and Derivatives. Journal of the American Chemical Society 2008, 130 (36) , 12031-12037. https://doi.org/10.1021/ja804567h
    59. Barry M. Trost and Jia Xie. Palladium-Catalyzed Diastereo- and Enantioselective Wagner−Meerwein Shift: Control of Absolute Stereochemistry in the C−C Bond Migration Event. Journal of the American Chemical Society 2008, 130 (19) , 6231-6242. https://doi.org/10.1021/ja7111299
    60. Carmen Nájera and, José M. Sansano. Catalytic Asymmetric Synthesis of α-Amino Acids. Chemical Reviews 2007, 107 (11) , 4584-4671. https://doi.org/10.1021/cr050580o
    61. Barry M. Trost and, Jia Xie. Palladium-Catalyzed Asymmetric Ring Expansion of Allenylcyclobutanols:  An Asymmetric Wagner−Meerwein Shift. Journal of the American Chemical Society 2006, 128 (18) , 6044-6045. https://doi.org/10.1021/ja0602501
    62. Takahiro Nishimura,, Sho Hirabayashi,, Yuichi Yasuhara, and, Tamio Hayashi. Rhodium-Catalyzed Asymmetric Hydroarylation of Diphenylphosphinylallenes with Arylboronic Acids. Journal of the American Chemical Society 2006, 128 (8) , 2556-2557. https://doi.org/10.1021/ja058763f
    63. Shengming Ma,, Zhenhua Gu, and, Zhanqian Yu. Pd(CH3CN)2Cl2-Catalyzed Oxidative Heterodimerization Reaction of 2,3-Allenamides and 1,2-Allenyl Ketones:  An Efficient Synthesis of 4-(Furan-3‘-yl)-2(5H)-furanimines. The Journal of Organic Chemistry 2005, 70 (16) , 6291-6294. https://doi.org/10.1021/jo0507441
    64. Shengming Ma. Some Typical Advances in the Synthetic Applications of Allenes. Chemical Reviews 2005, 105 (7) , 2829-2872. https://doi.org/10.1021/cr020024j
    65. Andreas Leitner,, Jens Larsen,, Christian Steffens, and, John F. Hartwig. Palladium-Catalyzed Addition of Mono- and Dicarbonyl Compounds to Conjugated Dienes. The Journal of Organic Chemistry 2004, 69 (22) , 7552-7557. https://doi.org/10.1021/jo0490999
    66. Lutz F. Tietze,, Hiriyakkanavar Ila, and, Hubertus P. Bell. Enantioselective Palladium-Catalyzed Transformations. Chemical Reviews 2004, 104 (7) , 3453-3516. https://doi.org/10.1021/cr030700x
    67. Sape S. Kinderman,, René de Gelder,, Jan H. van Maarseveen,, Hans E. Schoemaker,, Henk Hiemstra, and, Floris P. J. T. Rutjes. Amidopalladation of Alkoxyallenes Applied in the Synthesis of an Enantiopure 1-Ethylquinolizidine Frog Alkaloid. Journal of the American Chemical Society 2004, 126 (13) , 4100-4101. https://doi.org/10.1021/ja039919j
    68. Zhuo‐Wei Xu, Shaozhong Wang. Access to Chiral O , O ‐Acetals Enabled by Palladium‐Catalyzed Asymmetric Addition of Oximes to Alkoxyallenes. Chemistry – A European Journal 2023, 29 (65) https://doi.org/10.1002/chem.202301883
    69. Ling Liao, Zhi-Peng Zhao, Bo-Ning Gu, Jin-Sheng Yu, Jian Zhou. Palladium-Catalyzed Hydroalkylation of Alkoxyallenes Using Monofluorinated Nucleophiles. Synthesis 2023, 55 (19) , 3090-3103. https://doi.org/10.1055/a-2096-6929
    70. Xian‐Xiao Chen, Hao Luo, Ye‐Wei Chen, Yang Liu, Zhi‐Tao He. Enantioselective Palladium‐Catalyzed Directed Migratory Allylation of Remote Dienes. Angewandte Chemie 2023, 135 (34) https://doi.org/10.1002/ange.202307628
    71. Xian‐Xiao Chen, Hao Luo, Ye‐Wei Chen, Yang Liu, Zhi‐Tao He. Enantioselective Palladium‐Catalyzed Directed Migratory Allylation of Remote Dienes. Angewandte Chemie International Edition 2023, 62 (34) https://doi.org/10.1002/anie.202307628
    72. Long Li, Shan Wang, Ajay Jakhar, Zhihui Shao. Pd-catalyzed functionalization of 1,3-enynes via alkylene-π-allylpalladium intermediates. Green Synthesis and Catalysis 2023, 4 (2) , 124-134. https://doi.org/10.1016/j.gresc.2022.12.006
    73. Jia-Feng Chen, Sajid Ur Rehman, Changkun Li. Cobalt-catalyzed regiodivergent hydrofunctionalization of allenes. Organic Chemistry Frontiers 2022, 9 (24) , 6869-6874. https://doi.org/10.1039/D2QO01153K
    74. Reza Dehghanpour Kalan, Kamran Amiri, Frank Rominger, Saeed Balalaie, Hamid Reza Bijanzadeh. Regio- and diastereoselective transition metal-free hydroalkylation of N -allenyl sulfonamides by push–pull 2-alkynylquinolines. Organic & Biomolecular Chemistry 2022, 20 (42) , 8269-8272. https://doi.org/10.1039/D2OB01362B
    75. Qinglong Zhang, Minghui Zhu, Weiwei Zi. Synergizing palladium with Lewis base catalysis for stereodivergent coupling of 1,3-dienes with pentafluorophenyl acetates. Chem 2022, 8 (10) , 2784-2796. https://doi.org/10.1016/j.chempr.2022.07.014
    76. Gianpiero Cera, Giovanni Maestri. Palladium/Brønsted Acid Catalysis for Hydrofunctionalizations of Alkynes: From Tsuji‐Trost Allylations to Stereoselective Methodologies. ChemCatChem 2022, 14 (16) https://doi.org/10.1002/cctc.202200295
    77. Minghui Zhu, Peixin Wang, Qinglong Zhang, Wenjun Tang, Weiwei Zi. Diastereodivergent Aldol‐Type Coupling of Alkoxyallenes with Pentafluorophenyl Esters Enabled by Synergistic Palladium/Chiral Lewis Base Catalysis. Angewandte Chemie 2022, 134 (33) https://doi.org/10.1002/ange.202207621
    78. Minghui Zhu, Peixin Wang, Qinglong Zhang, Wenjun Tang, Weiwei Zi. Diastereodivergent Aldol‐Type Coupling of Alkoxyallenes with Pentafluorophenyl Esters Enabled by Synergistic Palladium/Chiral Lewis Base Catalysis. Angewandte Chemie International Edition 2022, 61 (33) https://doi.org/10.1002/anie.202207621
    79. Hua‐Chen Lin, Gary J. Knox, Colin M. Pearson, Chao Yang, Veronica Carta, Thomas N. Snaddon. A Pd−H/Isothiourea Cooperative Catalysis Approach to anti ‐Aldol Motifs: Enantioselective α‐Alkylation of Esters with Oxyallenes**. Angewandte Chemie 2022, 134 (25) https://doi.org/10.1002/ange.202201753
    80. Hua‐Chen Lin, Gary J. Knox, Colin M. Pearson, Chao Yang, Veronica Carta, Thomas N. Snaddon. A Pd−H/Isothiourea Cooperative Catalysis Approach to anti ‐Aldol Motifs: Enantioselective α‐Alkylation of Esters with Oxyallenes**. Angewandte Chemie International Edition 2022, 61 (25) https://doi.org/10.1002/anie.202201753
    81. Weiwei Chai, Bin Guo, Qinglong Zhang, Weiwei Zi. Cooperative Pd/Cu-catalyzed diastereodivergent coupling of allenamides and aldimine esters to access the Mannich-type motifs. Chem Catalysis 2022, 2 (6) , 1428-1439. https://doi.org/10.1016/j.checat.2022.04.006
    82. Maosheng He, Jinlong Zhang, Cong Zhang, Hao-Yang Wang, Gaoxi Jiang. Brønsted Acid Catalyzed Direct Annulation of Alkoxyallenes and Naphthols to Chroman Ketals. Synthesis 2022, 54 (09) , 2148-2156. https://doi.org/10.1055/s-0040-1719892
    83. Zhiping Yang, Jun (Joelle) Wang. Enantioselective Palladium‐Catalyzed Hydrophosphinylation of Allenes with Phosphine Oxides: Access to Chiral Allylic Phosphine Oxides. Angewandte Chemie 2021, 133 (52) , 27494-27498. https://doi.org/10.1002/ange.202112285
    84. Zhiping Yang, Jun (Joelle) Wang. Enantioselective Palladium‐Catalyzed Hydrophosphinylation of Allenes with Phosphine Oxides: Access to Chiral Allylic Phosphine Oxides. Angewandte Chemie International Edition 2021, 60 (52) , 27288-27292. https://doi.org/10.1002/anie.202112285
    85. Long Li, Shan Wang, Pengfei Luo, Ran Wang, Zheng Wang, Xiaoguang Li, Yuhua Deng, Fangzhi Peng, Zhihui Shao. Direct access to spirocycles by Pd/WingPhos-catalyzed enantioselective cycloaddition of 1,3-enynes. Nature Communications 2021, 12 (1) https://doi.org/10.1038/s41467-021-25981-x
    86. Dong‐Jin Jang, Sukhyun Lee, Juyeol Lee, Dohyun Moon, Young Ho Rhee. Palladium‐Catalyzed Asymmetric Decarboxylative Addition of β‐Keto Acids to Heteroatom‐Substituted Allenes. Angewandte Chemie 2021, 133 (41) , 22340-22345. https://doi.org/10.1002/ange.202107990
    87. Dong‐Jin Jang, Sukhyun Lee, Juyeol Lee, Dohyun Moon, Young Ho Rhee. Palladium‐Catalyzed Asymmetric Decarboxylative Addition of β‐Keto Acids to Heteroatom‐Substituted Allenes. Angewandte Chemie International Edition 2021, 60 (41) , 22166-22171. https://doi.org/10.1002/anie.202107990
    88. Joshua D. Sieber, Raphael K. Klake, Toolika Agrawal, Dang Binh Ho, Samantha L. Gargaro, Stephen Collins, Mytia D. Edwards. Cross‐Coupling of Allenamides and C ‐Based Nucleophiles by Pd‐Catalyzed Allylic Alkylation. Israel Journal of Chemistry 2021, 61 (5-6) , 332-339. https://doi.org/10.1002/ijch.202000096
    89. Wen‐Shuang Jiang, Ding‐Wei Ji, Wei‐Song Zhang, Gong Zhang, Xiang‐Ting Min, Yan‐Cheng Hu, Xu‐Liang Jiang, Qing‐An Chen. Orthogonal Regulation of Nucleophilic and Electrophilic Sites in Pd‐Catalyzed Regiodivergent Couplings between Indazoles and Isoprene. Angewandte Chemie 2021, 133 (15) , 8402-8409. https://doi.org/10.1002/ange.202100137
    90. Wen‐Shuang Jiang, Ding‐Wei Ji, Wei‐Song Zhang, Gong Zhang, Xiang‐Ting Min, Yan‐Cheng Hu, Xu‐Liang Jiang, Qing‐An Chen. Orthogonal Regulation of Nucleophilic and Electrophilic Sites in Pd‐Catalyzed Regiodivergent Couplings between Indazoles and Isoprene. Angewandte Chemie International Edition 2021, 60 (15) , 8321-8328. https://doi.org/10.1002/anie.202100137
    91. Minghui Zhu, Qinglong Zhang, Weiwei Zi. Diastereodivergent Synthesis of β‐Amino Alcohols by Dual‐Metal‐Catalyzed Coupling of Alkoxyallenes with Aldimine Esters. Angewandte Chemie 2021, 133 (12) , 6619-6626. https://doi.org/10.1002/ange.202014510
    92. Minghui Zhu, Qinglong Zhang, Weiwei Zi. Diastereodivergent Synthesis of β‐Amino Alcohols by Dual‐Metal‐Catalyzed Coupling of Alkoxyallenes with Aldimine Esters. Angewandte Chemie International Edition 2021, 60 (12) , 6545-6552. https://doi.org/10.1002/anie.202014510
    93. Min Liu, Haiying Zhao, Changkun Li. Rh(I)-catalyzed regio- and enantioselective allylic alkylation of Meldrum’s acid. Chinese Chemical Letters 2021, 32 (1) , 385-388. https://doi.org/10.1016/j.cclet.2020.04.009
    94. Guanlin Li, Xiaohong Huo, Xieyang Jiang, Wanbin Zhang. Asymmetric synthesis of allylic compounds via hydrofunctionalisation and difunctionalisation of dienes, allenes, and alkynes. Chemical Society Reviews 2020, 49 (7) , 2060-2118. https://doi.org/10.1039/C9CS00400A
    95. Haijian Yang, Dong Xing. Palladium-catalyzed diastereo- and enantioselective allylic alkylation of oxazolones with 1,3-dienes under base-free conditions. Chemical Communications 2020, 56 (26) , 3721-3724. https://doi.org/10.1039/D0CC00265H
    96. Jean Le Bras, Jacques Muzart. Pd-catalyzed reactions of cyclopropanols, cyclobutanols and cyclobutenols. Tetrahedron 2020, 76 (12) , 130879. https://doi.org/10.1016/j.tet.2019.130879
    97. Volker Martin Schmiedel, Hans-Ulrich Reissig. Alkoxyallenes as Starting Materials for the Syntheses of Natural Products. Current Organic Chemistry 2020, 23 (27) , 2976-3003. https://doi.org/10.2174/1385272824666191218115731
    98. Xiao‐Ye Yu, Wen‐Jing Xiao, Jia‐Rong Chen. Synthesis of Trisubstituted 1,2,4‐Triazoles from Azlactones and Aryldiazonium Salts by a Cycloaddition/Decarboxylation Cascade. European Journal of Organic Chemistry 2019, 2019 (41) , 6994-6998. https://doi.org/10.1002/ejoc.201901467
    99. Sangjune Park, Nathan J. Adamson, Steven J. Malcolmson. Brønsted acid and Pd–PHOX dual-catalysed enantioselective addition of activated C-pronucleophiles to internal dienes. Chemical Science 2019, 10 (19) , 5176-5182. https://doi.org/10.1039/C9SC00633H
    100. Jinlong Zhang, Lu Zhu, Kang Shen, Huameng Yang, Xiao-Chun Hang, Gaoxi Jiang. Brønsted acid-catalyzed aromatic annulation of alkoxyallenes with naphthols: a reaction sequence to larger π-conjugated naphthopyrans with aggregation-induced emission characters. Chemical Science 2019, 10 (4) , 1070-1074. https://doi.org/10.1039/C8SC03837F
    Load all citations

    Pair your accounts.

    Export articles to Mendeley

    Get article recommendations from ACS based on references in your Mendeley library.

    Pair your accounts.

    Export articles to Mendeley

    Get article recommendations from ACS based on references in your Mendeley library.

    You’ve supercharged your research process with ACS and Mendeley!

    STEP 1:
    Click to create an ACS ID

    Please note: If you switch to a different device, you may be asked to login again with only your ACS ID.

    Please note: If you switch to a different device, you may be asked to login again with only your ACS ID.

    Please note: If you switch to a different device, you may be asked to login again with only your ACS ID.

    MENDELEY PAIRING EXPIRED
    Your Mendeley pairing has expired. Please reconnect