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A Room-Temperature Catalytic Asymmetric Synthesis of Allenes with ECNU-Phos

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Shanghai Key Laboratory of Green Chemistry and Chemical Process, Department of Chemistry, East China Normal University, 3663 North Zhongshan Road, Shanghai 200062, China
State Key Laboratory of Organometallic Chemistry, Shanghai Institute of Organic Chemistry, Chinese Academy of Sciences, 345 Lingling Lu, Shanghai 200032, China
Cite this: J. Am. Chem. Soc. 2013, 135, 31, 11517–11520
Publication Date (Web):July 20, 2013
https://doi.org/10.1021/ja406135t
Copyright © 2013 American Chemical Society
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Abstract

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Three-carbon axial chirality has been asymmetrically established from racemic one-carbon central chirality efficiently at room temperature: we report here the discovery of the first catalytic asymmetric carbonylation of readily available racemic propargylic carbonates to access optically active 2,3-allenoates with fairly high ee. The combination of [(π-allyl)PdCl]2 with [(R)-ECNU-Phos], a new chiral bisphosphine ligand based on a biphenyl skeleton, demonstrates high enantioselectivity. Both enantiomers of allenoates can be obtained at room temperature by applying either (R)- or (S)-ECNU-Phos.

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  2. Huanan Wang, Hui Qian, Junliang Zhang, Shengming Ma. Catalytic Asymmetric Axially Chiral Allenyl C–P Bond Formation. Journal of the American Chemical Society 2022, 144 (28) , 12619-12626. https://doi.org/10.1021/jacs.2c04931
  3. Yao Tang, Guanzhao Wu, Shengzhou Jin, Yangxue Liu, Liulei Ma, Sai Zhang, Hossein Rouh, Ahmed I. M. Ali, Jia-Yin Wang, Ting Xu, Daniel Unruh, Kazimierz Surowiec, Guigen Li. From Center-to-Multilayer Chirality: Asymmetric Synthesis of Multilayer Targets with Electron-Rich Bridges. The Journal of Organic Chemistry 2022, 87 (9) , 5976-5986. https://doi.org/10.1021/acs.joc.2c00234
  4. Youxiang Jin, Hao Wen, Feiyan Yang, Decai Ding, Chuan Wang. Synthesis of Multisubstituted Allenes via Nickel-Catalyzed Cross-Electrophile Coupling. ACS Catalysis 2021, 11 (21) , 13355-13362. https://doi.org/10.1021/acscatal.1c04143
  5. Yidong Wang, Sarah G. Scrivener, Xiao-Dong Zuo, Ruihan Wang, Philip N. Palermo, Ethan Murphy, Austin C. Durham, Yi-Ming Wang. Iron-Catalyzed Contrasteric Functionalization of Allenic C(sp2)–H Bonds: Synthesis of α-Aminoalkyl 1,1-Disubstituted Allenes. Journal of the American Chemical Society 2021, 143 (37) , 14998-15004. https://doi.org/10.1021/jacs.1c07512
  6. Ronghua Lu, Tilong Yang, Xin Chen, Wenzheng Fan, Pinhong Chen, Zhenyang Lin, Guosheng Liu. Enantioselective Copper-Catalyzed Radical Cyanation of Propargylic C–H Bonds: Easy Access to Chiral Allenyl Nitriles. Journal of the American Chemical Society 2021, 143 (36) , 14451-14457. https://doi.org/10.1021/jacs.1c07190
  7. Thomas J. O’Connor, Binh Khanh Mai, Jordan Nafie, Peng Liu, F. Dean Toste. Generation of Axially Chiral Fluoroallenes through a Copper-Catalyzed Enantioselective β-Fluoride Elimination. Journal of the American Chemical Society 2021, 143 (34) , 13759-13768. https://doi.org/10.1021/jacs.1c05769
  8. Jiacheng Zhang, Xiaohong Huo, Junzhe Xiao, Ling Zhao, Shengming Ma, Wanbin Zhang. Enantio- and Diastereodivergent Construction of 1,3-Nonadjacent Stereocenters Bearing Axial and Central Chirality through Synergistic Pd/Cu Catalysis. Journal of the American Chemical Society 2021, 143 (32) , 12622-12632. https://doi.org/10.1021/jacs.1c05087
  9. Cheng-Yun Zhang, Jie Zhu, Su-Hang Cui, Xiao-Yu Xie, Xiao-Dong Wang, Lei Wu. Visible-Light-Induced 1,4-Hydroxysulfonylation of Vinyl Enynes with Sulfonyl Chlorides: The Bridge of Chloride Linking Water and Enynes. Organic Letters 2021, 23 (9) , 3530-3535. https://doi.org/10.1021/acs.orglett.1c00943
  10. Wen-Run Zhu, Qiong Su, Hong-Juan Diao, Er-Xuan Wang, Feng Wu, Yun-Long Zhao, Jiang Weng, Gui Lu. Enantioselective Dehydrative γ-Arylation of α-Indolyl Propargylic Alcohols with Phenols: Access to Chiral Tetrasubstituted Allenes and Naphthopyrans. Organic Letters 2020, 22 (17) , 6873-6878. https://doi.org/10.1021/acs.orglett.0c02386
  11. Calvin Q. O’Broin, Patrick J. Guiry. Advances in Decarboxylative Palladium-Catalyzed Reactions of Propargyl Electrophiles. The Journal of Organic Chemistry 2020, 85 (16) , 10321-10333. https://doi.org/10.1021/acs.joc.0c01218
  12. Huanan Wang, Hongwen Luo, Zhan-Ming Zhang, Wei-Feng Zheng, Yu Yin, Hui Qian, Junliang Zhang, Shengming Ma. Pd-Catalyzed Enantioselective Syntheses of Trisubstituted Allenes via Coupling of Propargylic Benzoates with Organoboronic Acids. Journal of the American Chemical Society 2020, 142 (21) , 9763-9771. https://doi.org/10.1021/jacs.0c02876
  13. Balú Cruz-Delgado, Ricardo I. Rodríguez, Anielka Rosado-Abón, Rubén Sánchez-Obregón, Francisco Yuste, José Alemán. Stereocontrolled Addition of Scrambling ortho-Sulfinyl Carbanions: Easy Access to Homopropargylamines and α-Allenylamines. Organic Letters 2020, 22 (6) , 2431-2436. https://doi.org/10.1021/acs.orglett.0c00625
  14. Chao Yang, Zheng-Li Liu, Dong-Ting Dai, Qi Li, Wei-Wei Ma, Meng Zhao, Yun-He Xu. Catalytic Asymmetric Conjugate Protosilylation and Protoborylation of 2-Trifluoromethyl Enynes for Synthesis of Functionalized Allenes. Organic Letters 2020, 22 (4) , 1360-1367. https://doi.org/10.1021/acs.orglett.9b04647
  15. Chenghao Zhu, Haoke Chu, Gen Li, Shengming Ma, Junliang Zhang. Pd-Catalyzed Enantioselective Heck Reaction of Aryl Triflates and Alkynes. Journal of the American Chemical Society 2019, 141 (49) , 19246-19251. https://doi.org/10.1021/jacs.9b10883
  16. Liela Bayeh-Romero, Stephen L. Buchwald. Copper Hydride Catalyzed Enantioselective Synthesis of Axially Chiral 1,3-Disubstituted Allenes. Journal of the American Chemical Society 2019, 141 (35) , 13788-13794. https://doi.org/10.1021/jacs.9b07582
  17. Zhi-Gang Ma, Jie-Lu Wei, Jun-Bing Lin, Guan-Jun Wang, Jia Zhou, Kai Chen, Chun-An Fan, Shu-Yu Zhang. Asymmetric Organocatalytic Synthesis of 2,3-Allenamides from Hydrogen-Bond-Stabilized Enynamides. Organic Letters 2019, 21 (7) , 2468-2472. https://doi.org/10.1021/acs.orglett.9b00839
  18. Xing-Feng Bai, Qiu-Chao Mu, Zheng Xu, Ke-Fang Yang, Li Li, Zhan-Jiang Zheng, Chun-Gu Xia, Li-Wen Xu. Catalytic Asymmetric Carbonylation of Prochiral Sulfonamides via C–H Desymmetrization. ACS Catalysis 2019, 9 (2) , 1431-1436. https://doi.org/10.1021/acscatal.8b04725
  19. Youming Huang, Juan del Pozo, Sebastian Torker, and Amir H. Hoveyda . Enantioselective Synthesis of Trisubstituted Allenyl–B(pin) Compounds by Phosphine–Cu-Catalyzed 1,3-Enyne Hydroboration. Insights Regarding Stereochemical Integrity of Cu–Allenyl Intermediates. Journal of the American Chemical Society 2018, 140 (7) , 2643-2655. https://doi.org/10.1021/jacs.7b13296
  20. Qi Liu, Xinjun Tang, Yujuan Cai, and Shengming Ma . Catalytic One-Pot Synthesis of Trisubstituted Allenes from Terminal Alkynes and Ketones. Organic Letters 2017, 19 (19) , 5174-5177. https://doi.org/10.1021/acs.orglett.7b02443
  21. Marie El Arba, Sara E. Dibrell, Ian T. Crouch, and Doug E. Frantz . Unified Approach to Substituted Allenoates via Pd-Catalyzed β-Hydride Elimination of (E)-Enol Triflates. Organic Letters 2017, 19 (19) , 5446-5449. https://doi.org/10.1021/acs.orglett.7b02736
  22. Yao Xu, Young J. Hong, Dean J. Tantillo, and M. Kevin Brown . Intramolecular Chirality Transfer [2 + 2] Cycloadditions of Allenoates and Alkenes. Organic Letters 2017, 19 (14) , 3703-3706. https://doi.org/10.1021/acs.orglett.7b01420
  23. Wen-Dao Chu, Lei Zhang, Zhikun Zhang, Qi Zhou, Fanyang Mo, Yan Zhang, and Jianbo Wang . Enantioselective Synthesis of Trisubstituted Allenes via Cu(I)-Catalyzed Coupling of Diazoalkanes with Terminal Alkynes. Journal of the American Chemical Society 2016, 138 (44) , 14558-14561. https://doi.org/10.1021/jacs.6b09674
  24. Hongyan Xiao, Yusuke Kobayashi, Yoshiji Takemoto, and Keiji Morokuma . Proton Transfer Mechanism of Organocatalyzed Isomerization of Alkynoates into Allenoates: Enantioselectivity and Reversibility. A DFT Study. ACS Catalysis 2016, 6 (5) , 2988-2996. https://doi.org/10.1021/acscatal.6b00038
  25. Gang Wang, Xiaohua Liu, Yushuang Chen, Jian Yang, Jun Li, Lili Lin, and Xiaoming Feng . Diastereoselective and Enantioselective Alleno-aldol Reaction of Allenoates with Isatins to Synthesis of Carbinol Allenoates Catalyzed by Gold. ACS Catalysis 2016, 6 (4) , 2482-2486. https://doi.org/10.1021/acscatal.6b00294
  26. Mariappan Periasamy, Polimera Obula Reddy, Iddum Satyanarayana, Lakavathu Mohan, and Athukuri Edukondalu . Diastereoselective Synthesis of Tetrasubstituted Propargylamines via Hydroamination and Metalation of 1-Alkynes and Their Enantioselective Conversion to Trisubstituted Chiral Allenes. The Journal of Organic Chemistry 2016, 81 (3) , 987-999. https://doi.org/10.1021/acs.joc.5b02554
  27. Devi Prasan Ojha and Kandikere Ramaiah Prabhu . Pd-Catalyzed Hydroborylation of Alkynes: A Ligand Controlled Regioselectivity Switch for the Synthesis of α- or β-Vinylboronates. Organic Letters 2016, 18 (3) , 432-435. https://doi.org/10.1021/acs.orglett.5b03416
  28. Min Wang, Zheng-Li Liu, Xiang Zhang, Pan-Pan Tian, Yun-He Xu, and Teck-Peng Loh . Synthesis of Highly Substituted Racemic and Enantioenriched Allenylsilanes via Copper-Catalyzed Hydrosilylation of (Z)-2-Alken-4-ynoates with Silylboronate. Journal of the American Chemical Society 2015, 137 (47) , 14830-14833. https://doi.org/10.1021/jacs.5b08279
  29. Can Zhu, Bin Yang, and Jan-E. Bäckvall . Highly Selective Cascade C–C Bond Formation via Palladium- Catalyzed Oxidative Carbonylation–Carbocyclization–Carbonylation–Alkynylation of Enallenes. Journal of the American Chemical Society 2015, 137 (37) , 11868-11871. https://doi.org/10.1021/jacs.5b06828
  30. Melih Kuş, Levent Artok, and Muhittin Aygün . Palladium-Catalyzed Alkoxycarbonylation of Conjugated Enyne Oxiranes: A Diastereoselective Method for the Synthesis of 7-Hydroxy-2,3,5-trienoates. The Journal of Organic Chemistry 2015, 80 (11) , 5494-5506. https://doi.org/10.1021/acs.joc.5b00382
  31. Liu Yang, Huayu Zheng, Lei Luo, Jiang Nan, Jingjing Liu, Yaoyu Wang, and Xinjun Luan . Palladium-Catalyzed Dynamic Kinetic Asymmetric Transformation of Racemic Biaryls: Axial-to-Central Chirality Transfer. Journal of the American Chemical Society 2015, 137 (15) , 4876-4879. https://doi.org/10.1021/jacs.5b01285
  32. Pauline Quinio, Cyril François, Ana Escribano Cuesta, Andreas K. Steib, Florian Achrainer, Hendrik Zipse, Konstantin Karaghiosoff, and Paul Knochel . Preparation of Tri- and Tetrasubstituted Allenes via Regioselective Lateral Metalation of Benzylic (Trimethylsilyl)alkynes Using TMPZnCl·LiCl. Organic Letters 2015, 17 (4) , 1010-1013. https://doi.org/10.1021/acs.orglett.5b00114
  33. Ezgi Şule Karagöz, Melih Kuş, Gürkan Eray Akpınar, and Levent Artok . Regio- and Stereoselective Synthesis of 2,3,5-Trienoates by Palladium-Catalyzed Alkoxycarbonylation of Conjugated Enyne Carbonates. The Journal of Organic Chemistry 2014, 79 (19) , 9222-9230. https://doi.org/10.1021/jo5014993
  34. Yu-Fei Ao, De-Xian Wang, Liang Zhao, and Mei-Xiang Wang . Biotransformations of Racemic 2,3-Allenenitriles in Biphasic Systems: Synthesis and Transformations of Enantioenriched Axially Chiral 2,3-Allenoic Acids and Their Derivatives. The Journal of Organic Chemistry 2014, 79 (7) , 3103-3110. https://doi.org/10.1021/jo500228z
  35. Robynne K. Neff and Doug E. Frantz . Recent Advances in the Catalytic Syntheses of Allenes: A Critical Assessment. ACS Catalysis 2014, 4 (2) , 519-528. https://doi.org/10.1021/cs401007m
  36. Hui Qian, Xiuzhao Yu, Junliang Zhang, and Jianwei Sun . Organocatalytic Enantioselective Synthesis of 2,3-Allenoates by Intermolecular Addition of Nitroalkanes to Activated Enynes. Journal of the American Chemical Society 2013, 135 (48) , 18020-18023. https://doi.org/10.1021/ja409080v
  37. Qiuyu Li, Yunchu Zhang, Pengyun Liu, Jing Zhong, Baihui Gong, Hequan Yao, Aijun Lin. Pd‐Catalyzed Asymmetric 5‐exo‐trig Cyclization/Cyclopropanation/Carbonylation of 1,6‐Enynes for the Construction of Chiral 3‐Azabicyclo[3.1.0]hexanes. Angewandte Chemie 2023, 135 (4) https://doi.org/10.1002/ange.202211988
  38. Qiuyu Li, Yunchu Zhang, Pengyun Liu, Jing Zhong, Baihui Gong, Hequan Yao, Aijun Lin. Pd‐Catalyzed Asymmetric 5‐exo‐trig Cyclization/Cyclopropanation/Carbonylation of 1,6‐Enynes for the Construction of Chiral 3‐Azabicyclo[3.1.0]hexanes. Angewandte Chemie International Edition 2023, 62 (4) https://doi.org/10.1002/anie.202211988
  39. Thien T. Nguyen. Organocatalytic synthesis of axially chiral tetrasubstituted allenes. Organic & Biomolecular Chemistry 2023, 21 (2) , 252-272. https://doi.org/10.1039/D2OB01794F
  40. Qi Li, Zi-Lu Wang, Yun-He Xu. Copper-catalyzed 1,4-protosilylation and 1,4-protoborylation of enynic orthoesters for synthesis of functionalized 2,3-allenoates. Chinese Chemical Letters 2023, 43 , 108150. https://doi.org/10.1016/j.cclet.2023.108150
  41. Jiayin Zhang, Xihao Chang, Xianghong Xu, Hongyi Wang, Lingzi Peng, Chang Guo. Nickel-catalyzed switchable 1,3-dienylation and enantioselective allenylation of phosphine oxides. Nature Communications 2022, 13 (1) https://doi.org/10.1038/s41467-022-34764-x
  42. Qi Liu, Jian Zheng, Xue Zhang, Shengming Ma. Photo and copper dual catalysis for allene syntheses from propargylic derivatives via one-electron process. Nature Communications 2022, 13 (1) https://doi.org/10.1038/s41467-022-30655-3
  43. Sailam Sri Gogula, Ramakrishna Konakalla, Kamalaker Reddy Kamireddy, Muralidar Reddy Puchakayala, Ch. Abraham Lincoln, Venkata Subba Reddy Basireddy. Diisobutylaluminium hydride mediated efficient synthesis of Morita–Baylis–Hilman adducts through α‐functionalization of alkyl propiolates. Journal of Heterocyclic Chemistry 2022, 5 https://doi.org/10.1002/jhet.4602
  44. Peng-Yu Liang, Shaoting Shi, Xin-Xin Xu, Hai-Rong Zhang, Zheng Che, Ka Lu, Chao-Xian Yan, Neng-Zhi Jin, Pan-Pan Zhou. Organocatalytic synthesis of chiral allene catalyzed by chiral phosphoric acid via asymmetric 1,8-addition of indole imine methide: Mechanism and origin of enantioselectivity. Molecular Catalysis 2022, 530 , 112648. https://doi.org/10.1016/j.mcat.2022.112648
  45. Krishna Yadavalli, Salvatore D. Lepore. Chiral Allenylcarbonyls – Underexploited Building Blocks for Complex Synthesis. Letters in Organic Chemistry 2022, 19 (8) , 597-601. https://doi.org/10.2174/1570178619666211231113033
  46. Hyun Jo Kim, Ji Eun Lee, Ganesh Koyyada, Mohan Lakavathu, Jae Hong Kim. 1,10‐Phenanthroline Copper(I) Complexes with A 3 Coupling to Access Allenes for Cycloaddition Reactions. Asian Journal of Organic Chemistry 2022, 11 (4) https://doi.org/10.1002/ajoc.202200053
  47. Jing-Yi Wang, Shuming Zhang, Xian-Yang Yu, Yu-Hao Wang, Hong-Lin Wan, Shu Zhang, Wei Tan, Feng Shi. Organocatalytic asymmetric synthesis of bioactive hexahydropyrrolo[2,3-b]indole-containing tetrasubstituted allenes bearing multiple chiral elements. Tetrahedron Chem 2022, 1 , 100007. https://doi.org/10.1016/j.tchem.2022.100007
  48. Jin-Bao Peng, Xin-Lian Liu, Lin Li, Xiao-Feng Wu. Palladium-catalyzed enantioselective carbonylation reactions. Science China Chemistry 2022, 65 (3) , 441-461. https://doi.org/10.1007/s11426-021-1165-6
  49. Jinbo Zhao, Yunhe Xu. Asymmetric Synthesis of Chiral Allenes. 2021, 141-172. https://doi.org/10.1002/9783527825172.ch6
  50. Kai Luo, Yuan Li, Zitong Fu, Ling Zhang, Zhipeng Wang, Jiangyan Xu, Bingjun Yu, Lei Wu. Transition‐Metal‐Free Cascade Enyne Rearrangement and Cyclopropanation of Allenylphosphine Oxides with N ‐Tosylhydrazones Accessing Alkynylcyclopropane Derivatives. Advanced Synthesis & Catalysis 2021, 363 (17) , 4222-4228. https://doi.org/10.1002/adsc.202100392
  51. Yongtao Xie, Xing Yang, Jun Xu, Huifang Chai, Hongxia Liu, Junmin Zhang, Jun Song, Yuan Gao, Zhichao Jin, Yonggui Robin Chi. Access to Allene‐Containing Molecules via Enantioselective Reactions of Azolium Cumulenolate Intermediates. Angewandte Chemie 2021, 133 (27) , 14943-14949. https://doi.org/10.1002/ange.202102177
  52. Yongtao Xie, Xing Yang, Jun Xu, Huifang Chai, Hongxia Liu, Junmin Zhang, Jun Song, Yuan Gao, Zhichao Jin, Yonggui Robin Chi. Access to Allene‐Containing Molecules via Enantioselective Reactions of Azolium Cumulenolate Intermediates. Angewandte Chemie International Edition 2021, 60 (27) , 14817-14823. https://doi.org/10.1002/anie.202102177
  53. Ben Niu, Yin Wei, Min Shi. Palladium catalyzed divergent cycloadditions of vinylidenecyclopropane-diesters with methyleneindolinones enabled by zwitterionic π-propargyl palladium species. Chemical Communications 2021, 57 (39) , 4783-4786. https://doi.org/10.1039/D1CC01453F
  54. Ben Niu, Yin Wei, Min Shi. Recent advances in annulation reactions based on zwitterionic π-allyl palladium and propargyl palladium complexes. Organic Chemistry Frontiers 2021, 4 https://doi.org/10.1039/D1QO00273B
  55. Cheng-Yu He, Yun-Xuan Tan, Xin Wang, Rui Ding, Yi-Fan Wang, Feng Wang, Dingding Gao, Ping Tian, Guo-Qiang Lin. Copper(I)-catalyzed diastereo- and enantio-selective construction of optically pure exocyclic allenes. Nature Communications 2020, 11 (1) https://doi.org/10.1038/s41467-020-18136-x
  56. Jiawen Wang, Sujuan Zheng, Subramani Rajkumar, Jinglei Xie, Na Yu, Qian Peng, Xiaoyu Yang. Chiral phosphoric acid-catalyzed stereodivergent synthesis of trisubstituted allenes and computational mechanistic studies. Nature Communications 2020, 11 (1) https://doi.org/10.1038/s41467-020-19294-8
  57. Yimin Hu, Wangyu Shi, Bing Zheng, Jianning Liao, Wei Wang, Yongjun Wu, Hongchao Guo. Organocatalytic Asymmetric C(sp 2 )−H Allylic Alkylation: Enantioselective Synthesis of Tetrasubstituted Allenoates. Angewandte Chemie 2020, 132 (45) , 19992-19996. https://doi.org/10.1002/ange.202009460
  58. Yimin Hu, Wangyu Shi, Bing Zheng, Jianning Liao, Wei Wang, Yongjun Wu, Hongchao Guo. Organocatalytic Asymmetric C(sp 2 )−H Allylic Alkylation: Enantioselective Synthesis of Tetrasubstituted Allenoates. Angewandte Chemie International Edition 2020, 59 (45) , 19820-19824. https://doi.org/10.1002/anie.202009460
  59. Shihua Song, Shengming Ma. Highly Selective Nucleophilic 4‐Aryl ‐2,3‐allenylation of Malonates †. Chinese Journal of Chemistry 2020, 38 (11) , 1233-1238. https://doi.org/10.1002/cjoc.202000300
  60. Xingguang Li, Jianwei Sun. Organocatalytic Enantioselective Synthesis of Chiral Allenes: Remote Asymmetric 1,8‐Addition of Indole Imine Methides. Angewandte Chemie 2020, 132 (39) , 17197-17202. https://doi.org/10.1002/ange.202006137
  61. Xingguang Li, Jianwei Sun. Organocatalytic Enantioselective Synthesis of Chiral Allenes: Remote Asymmetric 1,8‐Addition of Indole Imine Methides. Angewandte Chemie International Edition 2020, 59 (39) , 17049-17054. https://doi.org/10.1002/anie.202006137
  62. Ming Chen, Xucai Wang, Pengfei Yang, Xun Kou, Zhi‐Hui Ren, Zheng‐Hui Guan. Palladium‐Catalyzed Enantioselective Heck Carbonylation with a Monodentate Phosphoramidite Ligand: Asymmetric Synthesis of (+)‐Physostigmine, (+)‐Physovenine, and (+)‐Folicanthine. Angewandte Chemie 2020, 132 (29) , 12297-12303. https://doi.org/10.1002/ange.202003288
  63. Ming Chen, Xucai Wang, Pengfei Yang, Xun Kou, Zhi‐Hui Ren, Zheng‐Hui Guan. Palladium‐Catalyzed Enantioselective Heck Carbonylation with a Monodentate Phosphoramidite Ligand: Asymmetric Synthesis of (+)‐Physostigmine, (+)‐Physovenine, and (+)‐Folicanthine. Angewandte Chemie International Edition 2020, 59 (29) , 12199-12205. https://doi.org/10.1002/anie.202003288
  64. Chunyin Law, Elton Kativhu, Johnny Wang, James P. Morken. Diastereo‐ and Enantioselective 1,4‐Difunctionalization of Borylenynes by Catalytic Conjunctive Cross‐Coupling. Angewandte Chemie 2020, 132 (26) , 10397-10401. https://doi.org/10.1002/ange.202001580
  65. Chunyin Law, Elton Kativhu, Johnny Wang, James P. Morken. Diastereo‐ and Enantioselective 1,4‐Difunctionalization of Borylenynes by Catalytic Conjunctive Cross‐Coupling. Angewandte Chemie International Edition 2020, 59 (26) , 10311-10315. https://doi.org/10.1002/anie.202001580
  66. Feng Zhong, Qi‐Yan Xue, Liang Yin. Construction of Chiral 2,3‐Allenols through a Copper(I)‐Catalyzed Asymmetric Direct Alkynylogous Aldol Reaction. Angewandte Chemie 2020, 132 (4) , 1578-1582. https://doi.org/10.1002/ange.201912140
  67. Feng Zhong, Qi‐Yan Xue, Liang Yin. Construction of Chiral 2,3‐Allenols through a Copper(I)‐Catalyzed Asymmetric Direct Alkynylogous Aldol Reaction. Angewandte Chemie International Edition 2020, 59 (4) , 1562-1566. https://doi.org/10.1002/anie.201912140
  68. Junxian Yang, Zheng Wang, Zeyuan He, Guofeng Li, Liang Hong, Wangsheng Sun, Rui Wang. Organocatalytic Enantioselective Synthesis of Tetrasubstituted α‐Amino Allenoates by Dearomative γ‐Addition of 2,3‐Disubstituted Indoles to β,γ‐Alkynyl‐α‐imino Esters. Angewandte Chemie 2020, 132 (2) , 652-657. https://doi.org/10.1002/ange.201911420
  69. Junxian Yang, Zheng Wang, Zeyuan He, Guofeng Li, Liang Hong, Wangsheng Sun, Rui Wang. Organocatalytic Enantioselective Synthesis of Tetrasubstituted α‐Amino Allenoates by Dearomative γ‐Addition of 2,3‐Disubstituted Indoles to β,γ‐Alkynyl‐α‐imino Esters. Angewandte Chemie International Edition 2020, 59 (2) , 642-647. https://doi.org/10.1002/anie.201911420
  70. Shihua Song, Jing Zhou, Chunling Fu, Shengming Ma. Catalytic enantioselective construction of axial chirality in 1,3-disubstituted allenes. Nature Communications 2019, 10 (1) https://doi.org/10.1038/s41467-018-07908-1
  71. Wei-Feng Zheng, Wanli Zhang, Chaofan Huang, Penglin Wu, Hui Qian, Lei Wang, Yin-Long Guo, Shengming Ma. Tetrasubstituted allenes via the palladium-catalysed kinetic resolution of propargylic alcohols using a supporting ligand. Nature Catalysis 2019, 2 (11) , 997-1005. https://doi.org/10.1038/s41929-019-0346-z
  72. Huaanzi Hu, Fan Teng, Jian Liu, Weiming Hu, Shuang Luo, Qiang Zhu. Enantioselective Synthesis of 2‐Oxindole Spirofused Lactones and Lactams by Heck/Carbonylative Cylization Sequences: Method Development and Applications. Angewandte Chemie 2019, 131 (27) , 9323-9327. https://doi.org/10.1002/ange.201904838
  73. Huaanzi Hu, Fan Teng, Jian Liu, Weiming Hu, Shuang Luo, Qiang Zhu. Enantioselective Synthesis of 2‐Oxindole Spirofused Lactones and Lactams by Heck/Carbonylative Cylization Sequences: Method Development and Applications. Angewandte Chemie International Edition 2019, 58 (27) , 9225-9229. https://doi.org/10.1002/anie.201904838
  74. Ina Scheipers, Christian Mück‐Lichtenfeld, Armido Studer. Palladiumkatalysierte decarboxylierende γ‐Arylierung: Ein Zugang zu tetrasubstituierten chiralen Allenen. Angewandte Chemie 2019, 131 (20) , 6616-6620. https://doi.org/10.1002/ange.201901848
  75. Ina Scheipers, Christian Mück‐Lichtenfeld, Armido Studer. Palladium‐Catalyzed Decarboxylative γ‐Arylation for the Synthesis of Tetrasubstituted Chiral Allenes. Angewandte Chemie International Edition 2019, 58 (20) , 6545-6548. https://doi.org/10.1002/anie.201901848
  76. Xiao-Feng Wei, Takayuki Wakaki, Taisuke Itoh, Hong-Liang Li, Takayoshi Yoshimura, Aya Miyazaki, Kounosuke Oisaki, Miho Hatanaka, Yohei Shimizu, Motomu Kanai. Catalytic Regio- and Enantioselective Proton Migration from Skipped Enynes to Allenes. Chem 2019, 5 (3) , 585-599. https://doi.org/10.1016/j.chempr.2018.11.022
  77. Yuan Yao, Guirong Zhu, Qin Chen, Hui Qian, Shengming Ma. Efficient synthesis of tetrasubstituted 2,3-allenoates and preliminary studies on bioactivities. Organic Chemistry Frontiers 2019, 6 (3) , 304-308. https://doi.org/10.1039/C8QO01202D
  78. Songjie Yu, Hui Leng Sang, Shuo-Qing Zhang, Xin Hong, Shaozhong Ge. Catalytic asymmetric synthesis of chiral trisubstituted heteroaromatic allenes from 1,3-enynes. Communications Chemistry 2018, 1 (1) https://doi.org/10.1038/s42004-018-0065-4
  79. Barry M. Trost, Daniel Zell, Christoph Hohn, Guillaume Mata, Autumn Maruniak. Enantio- and Diastereoselective Synthesis of Chiral Allenes by Palladium-Catalyzed Asymmetric [3+2] Cycloaddition Reactions. Angewandte Chemie 2018, 130 (39) , 13098-13102. https://doi.org/10.1002/ange.201808345
  80. Barry M. Trost, Daniel Zell, Christoph Hohn, Guillaume Mata, Autumn Maruniak. Enantio- and Diastereoselective Synthesis of Chiral Allenes by Palladium-Catalyzed Asymmetric [3+2] Cycloaddition Reactions. Angewandte Chemie International Edition 2018, 57 (39) , 12916-12920. https://doi.org/10.1002/anie.201808345
  81. Pablo Domingo-Legarda, Rita Soler-Yanes, M. Teresa Quirós-López, Elena Buñuel, Diego J. Cárdenas. Iron-Catalyzed Coupling of Propargyl Bromides and Alkyl Grignard Reagents. European Journal of Organic Chemistry 2018, 2018 (35) , 4900-4904. https://doi.org/10.1002/ejoc.201800849
  82. Xuebei Shao, Chang Wen, Gang Zhang, Kangping Cao, Ling Wu, Qinghan Li. Palladium-catalyzed, ligand-free S N 2’ substitution reactions of organoaluminum with propargyl acetates for the synthesis of multi-substituted allenes. Journal of Organometallic Chemistry 2018, 870 , 68-75. https://doi.org/10.1016/j.jorganchem.2018.06.020
  83. Pernille H. Poulsen, Yang Li, Vibeke H. Lauridsen, Danny K. B. Jørgensen, Teresa A. Palazzo, Marta Meazza, Karl Anker Jørgensen. Organocatalytic Formation of Chiral Trisubstituted Allenes and Chiral Furan Derivatives. Angewandte Chemie 2018, 130 (33) , 10821-10825. https://doi.org/10.1002/ange.201806238
  84. Pernille H. Poulsen, Yang Li, Vibeke H. Lauridsen, Danny K. B. Jørgensen, Teresa A. Palazzo, Marta Meazza, Karl Anker Jørgensen. Organocatalytic Formation of Chiral Trisubstituted Allenes and Chiral Furan Derivatives. Angewandte Chemie International Edition 2018, 57 (33) , 10661-10665. https://doi.org/10.1002/anie.201806238
  85. Yu Tang, Jian Xu, Jian Yang, Lili Lin, Xiaoming Feng, Xiaohua Liu. Asymmetric Three-Component Reaction for the Synthesis of Tetrasubstituted Allenoates via Allenoate-Copper Intermediates. Chem 2018, 4 (7) , 1658-1672. https://doi.org/10.1016/j.chempr.2018.04.012
  86. Fırat Ziyanak, Melih Kuş, Leman Alkan-Karadeniz, Levent Artok. Palladium-catalysed reactions of conjugated enyne oxiranes with organoborons: A diastereoselective method of the synthesis of 2,4,5-trienol derivatives. Tetrahedron 2018, 74 (27) , 3652-3662. https://doi.org/10.1016/j.tet.2018.05.030
  87. Shenci Lu, Jun-Yang Ong, Si Bei Poh, Terence Tsang, Yu Zhao. Transition-Metal-Free Decarboxylative Propargylic Substitution/Cyclization with either Azolium Enolates or Acyl Anions. Angewandte Chemie 2018, 130 (20) , 5816-5821. https://doi.org/10.1002/ange.201801340
  88. Shenci Lu, Jun-Yang Ong, Si Bei Poh, Terence Tsang, Yu Zhao. Transition-Metal-Free Decarboxylative Propargylic Substitution/Cyclization with either Azolium Enolates or Acyl Anions. Angewandte Chemie International Edition 2018, 57 (20) , 5714-5719. https://doi.org/10.1002/anie.201801340
  89. Jianxin Dai, Xinyu Duan, Jing Zhou, Chunling Fu, Shengming Ma. Catalytic Enantioselective Simultaneous Control of Axial Chirality and Central Chirality in Allenes. Chinese Journal of Chemistry 2018, 36 (5) , 387-391. https://doi.org/10.1002/cjoc.201800090
  90. Xue Bei Shao, Zhen Zhang, Qing Han Li, Zhi Gang Zhao. Synthesis of multi-substituted allenes from organoalane reagents and propargyl esters by using a nickel catalyst. Organic & Biomolecular Chemistry 2018, 16 (26) , 4797-4806. https://doi.org/10.1039/C8OB00781K
  91. Wei-Feng Zheng, Wanli Zhang, Jianhao Huang, Yibo Yu, Hui Qian, Shengming Ma. 2,3-Allenoic acids via palladium-catalyzed carboxylation of propargylic alcohols. Organic Chemistry Frontiers 2018, 5 (12) , 1900-1904. https://doi.org/10.1039/C8QO00318A
  92. Deyun Qian, LinLin Wu, Zhenyang Lin, Jianwei Sun. Organocatalytic synthesis of chiral tetrasubstituted allenes from racemic propargylic alcohols. Nature Communications 2017, 8 (1) https://doi.org/10.1038/s41467-017-00251-x
  93. Zeng-Wei Lai, Chuan Liu, Hongbin Sun, Shu-Li You. Asymmetric Synthesis of 3-Allyloxindoles and 3-Allenyloxindoles by Scandium(III)-Catalyzed Claisen Rearrangement Reactions. Chinese Journal of Chemistry 2017, 35 (10) , 1512-1516. https://doi.org/10.1002/cjoc.201700486
  94. Wanli Zhang, Shengming Ma. Palladium-Catalyzed Enantioselective Alkoxycarbonylation of Propargylic Carbonates with ( R )- or ( S )-3,4,5-(MeO) 3 -MeOBIPHEP. Chemistry - A European Journal 2017, 23 (36) , 8590-8595. https://doi.org/10.1002/chem.201701194
  95. Jian-Siang Poh, Szabolcs Makai, Timo von Keutz, Duc N. Tran, Claudio Battilocchio, Patrick Pasau, Steven V. Ley. Rapid Asymmetric Synthesis of Disubstituted Allenes by Coupling of Flow-Generated Diazo Compounds and Propargylated Amines. Angewandte Chemie 2017, 129 (7) , 1890-1894. https://doi.org/10.1002/ange.201611067
  96. Jian-Siang Poh, Szabolcs Makai, Timo von Keutz, Duc N. Tran, Claudio Battilocchio, Patrick Pasau, Steven V. Ley. Rapid Asymmetric Synthesis of Disubstituted Allenes by Coupling of Flow-Generated Diazo Compounds and Propargylated Amines. Angewandte Chemie International Edition 2017, 56 (7) , 1864-1868. https://doi.org/10.1002/anie.201611067
  97. Rita Soler-Yanes, Iván Arribas-Álvarez, Manuel Guisán-Ceinos, Elena Buñuel, Diego J. Cárdenas. Ni I Catalyzes the Regioselective Cross-Coupling of Alkylzinc Halides and Propargyl Bromides to Allenes. Chemistry - A European Journal 2017, 23 (7) , 1584-1590. https://doi.org/10.1002/chem.201603758
  98. Wanli Zhang, Chaofan Huang, Yuan Yuan, Shengming Ma. Catalytic transient leaving group for atom-economic synthesis of allenes from 2-alkynols. Chemical Communications 2017, 53 (92) , 12430-12433. https://doi.org/10.1039/C7CC06866B
  99. Wen-Dao Chu, Yan Zhang, Jianbo Wang. Recent advances in catalytic asymmetric synthesis of allenes. Catalysis Science & Technology 2017, 7 (20) , 4570-4579. https://doi.org/10.1039/C7CY01319A
  100. Theresa M. Locascio, Jon A. Tunge. Palladium-Catalyzed Regiodivergent Substitution of Propargylic Carbonates. Chemistry - A European Journal 2016, 22 (50) , 18140-18146. https://doi.org/10.1002/chem.201603481
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