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Enantioselective Synthesis of Chiral β2-Amino Phosphorus Derivatives via Nickel-Catalyzed Asymmetric Hydrogenation Научная публикация

Журнал Journal of the American Chemical Society
ISSN: 0002-7863 , E-ISSN: 1520-5126
Вых. Данные Год: 2025, Том: 147, Номер: 1, Страницы: 342–352 Страниц : DOI: 10.1021/jacs.4c10623
Авторы Wei Hanlin 1 , Luo Yicong 1 , Li Jinhui 1 , Chen Jianzhong 1 , Gridnev Ilya D. 2 , Zhang Wanbin 1
Организации
1 Shanghai Key Laboratory for Molecular Engineering of Chiral Drugs, Frontiers Science Center for Transformative Molecules, School of Chemistry and Chemical Engineering, Shanghai Jiao Tong University, 800 Dongchuan Road, Shanghai 200240, China
2 N.D. Zelinsky Institute of Organic Chemistry, Russian Academy of Sciences, Leninsky Prospekt 47, Moscow 119991, Russian Federation

Реферат: Compared with chiral β3-amino phosphorus compounds, which can be easily derived from natural optically pure α-amino acids, obtaining chiral β2-amino phosphorus derivatives remains a challenge. These derivatives, which cannot be derived from chiral natural amino acids, possess unique biological activities or potential catalytic activities. Herein, highly enantioselective hydrogenation for the preparation of chiral β2-amino phosphorus derivatives from E-β-enamido phosphorus compounds is reported by using a green and low-cost earth-abundant metal nickel catalyst (13 examples of 99% ee). In particular, this catalytic system provides the same enantiomer product from the E- and Z-alkene substrates, and the E/Z-substrate mixtures provide good results (up to 96% ee). The products can be diversely derivatized, and the derivatives exhibit good catalytic activities as novel chiral β2-aminophosphine ligands. Density functional theory calculations reveal that the weak attractive interactions between the nickel catalyst and the substrate are crucial for achieving perfect enantioselectivities. In addition, the different coordination modes between the E- or Z-substrates and the catalyst may result in the formation of the same enantiomer product.
Библиографическая ссылка: Wei H. , Luo Y. , Li J. , Chen J. , Gridnev I.D. , Zhang W.
Enantioselective Synthesis of Chiral β2-Amino Phosphorus Derivatives via Nickel-Catalyzed Asymmetric Hydrogenation
Journal of the American Chemical Society. 2025. V.147. N1. P.342–352. DOI: 10.1021/jacs.4c10623 WOS OpenAlex
Идентификаторы БД:
Web of science: WOS:001387019900001
OpenAlex: W4405860114
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