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Palladium-Catalyzed Asymmetric Addition of Pronucleophiles to Allenes
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    Palladium-Catalyzed Asymmetric Addition of Pronucleophiles to Allenes
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    Department of Chemistry, Stanford University, Stanford, California 94305-5080
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    Journal of the American Chemical Society

    Cite this: J. Am. Chem. Soc. 2003, 125, 15, 4438–4439
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    https://doi.org/10.1021/ja029190z
    Published March 25, 2003
    Copyright © 2003 American Chemical Society

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    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.

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    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.

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    13. 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
    14. 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
    15. 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
    16. 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
    17. 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
    18. 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
    19. 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
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    21. 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
    22. 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
    23. 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
    24. 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
    25. 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
    26. 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
    27. 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
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    29. 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
    30. 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
    31. 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
    32. 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
    33. 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
    34. 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
    35. 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
    36. 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
    37. 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
    38. 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
    39. 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
    40. 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
    41. 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
    42. 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
    43. 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
    44. 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
    45. 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
    46. 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
    47. 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
    48. 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
    49. 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
    50. 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
    51. 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
    52. 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
    53. 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
    54. 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
    55. 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
    56. 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
    57. 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
    58. 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
    59. 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
    60. 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
    61. 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
    62. 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
    63. 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
    64. 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
    65. 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
    66. 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
    67. 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
    68. 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
    69. 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
    70. 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
    71. 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
    72. 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
    73. Shengming Ma. Some Typical Advances in the Synthetic Applications of Allenes. Chemical Reviews 2005, 105 (7) , 2829-2872. https://doi.org/10.1021/cr020024j
    74. 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
    75. 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
    76. 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
    77. Shiwen Liu, Zhibin Du, Wenbo Gong, Yuhao Yang, Changguang Yao, Xiaojun Zeng. Site‐Selective C‐Alkylation of Fluoroamides with Active Methylene Compounds. Asian Journal of Organic Chemistry 2025, 14 (4) https://doi.org/10.1002/ajoc.202400663
    78. Yixuan Zheng, Xinhao Deng, Fei Zhao, Yuanyuan Peng, Qiongjiao Yan, Wei Wang, Fener Chen, Hui Zhou. Pd-catalyzed asymmetric allylic alkylation of N -hydroxyphthalimide esters with allyl acetates. Organic Chemistry Frontiers 2025, 12 (5) , 1537-1542. https://doi.org/10.1039/D4QO02257B
    79. Ming‐Qiao Tang, Zi‐Jiang Yang, Ai‐Jun Han, Zhi‐Tao He. Diastereoselective and Enantioselective Hydrophosphinylations of Conjugated Enynes, Allenes and Dienes via Synergistic Pd/Co Catalysis. Angewandte Chemie International Edition 2025, 64 (1) https://doi.org/10.1002/anie.202413428
    80. Ming‐Qiao Tang, Zi‐Jiang Yang, Ai‐Jun Han, Zhi‐Tao He. Diastereoselective and Enantioselective Hydrophosphinylations of Conjugated Enynes, Allenes and Dienes via Synergistic Pd/Co Catalysis. Angewandte Chemie 2025, 137 (1) https://doi.org/10.1002/ange.202413428
    81. Akash Mishra, Stephen Hanessian. 1,2-trans-Diaminocyclohexane (DACH) in Asymmetric Catalysis: Nearing Fifty Years of Faithful Service and Counting. Synthesis 2024, 56 (18) , 2747-2885. https://doi.org/10.1055/s-0042-1751582
    82. Hao Zhang, Wei Wen, Yu-Yang Wang, Ze-Xi Lu, Jin-Long Liu, Zhu-Lian Wu, Tian Cai, Qi-Xiang Guo. Asymmetric bifunctionalization of allenes with aryl iodides and amino acids enabled by chiral aldehyde/palladium combined catalysis. Chemical Science 2024, 15 (32) , 12983-12988. https://doi.org/10.1039/D4SC03398A
    83. Jing‐Ming Zhang, Yu‐Chao Wang, Liang Chen, Chao Ma, Zhi‐Tao He. Stereoselective Synthesis of Polysubstituted Dihydropyrroles via 1,5‐Addition and N ‐1,4‐Addition Cascade. Chemistry – A European Journal 2024, 30 (38) https://doi.org/10.1002/chem.202401350
    84. Hao Guo, Jan‐Lukas Kirchhoff, Carsten Strohmann, Bastian Grabe, Charles C. J. Loh. Asymmetric Pd/Organoboron‐Catalyzed Site‐Selective Carbohydrate Functionalization with Alkoxyallenes Involving Noncovalent Stereocontrol. Angewandte Chemie 2024, 136 (21) https://doi.org/10.1002/ange.202400912
    85. Nan Jiang, Pei‐Zhi Liu, Zhi‐Zhou Pan, Si‐Qing Wang, Qian Peng, Liang Yin. Asymmetric Synthesis of Trisubstituted Vicinal Diols through Copper(I)‐Catalyzed Diastereoselective and Enantioselective Allylation of Ketones with Siloxypropadienes. Angewandte Chemie 2024, 136 (21) https://doi.org/10.1002/ange.202402195
    86. Hao Guo, Jan‐Lukas Kirchhoff, Carsten Strohmann, Bastian Grabe, Charles C. J. Loh. Asymmetric Pd/Organoboron‐Catalyzed Site‐Selective Carbohydrate Functionalization with Alkoxyallenes Involving Noncovalent Stereocontrol. Angewandte Chemie International Edition 2024, 63 (21) https://doi.org/10.1002/anie.202400912
    87. Nan Jiang, Pei‐Zhi Liu, Zhi‐Zhou Pan, Si‐Qing Wang, Qian Peng, Liang Yin. Asymmetric Synthesis of Trisubstituted Vicinal Diols through Copper(I)‐Catalyzed Diastereoselective and Enantioselective Allylation of Ketones with Siloxypropadienes. Angewandte Chemie International Edition 2024, 63 (21) https://doi.org/10.1002/anie.202402195
    88. Jiao Long, Yangyang Li, Guoyin Yin. Hydrometalation of C–C π-Bonds Followed by Cross-Coupling. 2024https://doi.org/10.1016/B978-0-323-96025-0.00102-2
    89. 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
    90. 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
    91. 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
    92. 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
    93. 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
    94. 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
    95. 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
    96. 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
    97. 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
    98. 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
    99. 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
    100. 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
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