Ni-Catalyzed enantioselective reductive aryl-alkenylation of alkenes: application to the synthesis of (+)-physovenine and (+)-physostigmine

被引：63

作者：

Li, Yuxiu ^{[1
]}

Ding, Zhengtian ^{[1
]}

Lei, Aiwen ^{[1
]}

Kong, Wangqing ^{[1
]}

机构：

[1] Wuhan Univ, Coll Chem & Mol Sci, IAS, Wuhan 430072, Hubei, Peoples R China

来源：

ORGANIC CHEMISTRY FRONTIERS | 2019年 / 6卷 / 18期

基金：

中国国家自然科学基金;

关键词：

CROSS-COUPLING REACTIONS; ANION CAPTURE PROCESSES; FORMAL TOTAL SYNTHESIS; ASYMMETRIC-SYNTHESIS; CALABAR ALKALOIDS; CYCLIZATION; OXINDOLES; HALIDES; ROUTE; DICARBOFUNCTIONALIZATION;

D O I：

10.1039/c9qo00744j

中图分类号：

O62 [有机化学];

学科分类号：

070303 ; 081704 ;

摘要：

A Ni-catalyzed enantioselective reductive aryl-alkenylation of alkenes by cyclizative coupling of an aryl bromide and a vinyl bromide is developed, providing efficient access to functionalized 3,3-disubstituted oxindoles under mild conditions, without requiring the use of preformed vinylmetallic reagents. With this method, a concise formal synthesis of (+)-physovenine and (+)-physostigmine has been completed.

引用

页码：3305 / 3309

页数：5

共 50 条

[1] Gold-Catalyzed Aryl-Alkenylation of Alkenes
Kumar, Anil
Das, Akash
Patil, Nitin T.
[J]. ORGANIC LETTERS, 2023, 25 (16) : 2934 - 2938
[2] Synthesis of Carbonyl-Containing Oxindoles via Ni-Catalyzed Reductive Aryl-Acylation and Aryl-Esterification of Alkenes
Ding, Zhengtian
Kong, Wangqing
[J]. MOLECULES, 2022, 27 (18):
[3] Ni-Catalyzed Reductive Difunctionalization of Alkenes
Ping, Yuanyuan
Kong, Wangqing
[J]. SYNTHESIS-STUTTGART, 2020, 52 (07): : 979 - 992
[4] Highly Enantioselective Cross-Electrophile Aryl-Alkenylation of Unactivated Alkenes
Tian, Zhi-Xiong
Qiao, Jin-Bao
Xu, Guang-Li
Pang, Xiaobo
Qi, Liangliang
Ma, Wei-Yuan
Zhao, Zhen-Zhen
Duan, Jicheng
Du, Yun-Fei
Su, Peifeng
Liu, Xue-Yuan
Shu, Xing-Zhong
[J]. JOURNAL OF THE AMERICAN CHEMICAL SOCIETY, 2019, 141 (18) : 7637 - 7643
[5] Ni-Catalyzed Reductive Arylcyanation of Alkenes
Li, Hengxu
Chen, Jiachang
Dong, Jueqi
Kong, Wangqing
[J]. ORGANIC LETTERS, 2021, 23 (16) : 6466 - 6470
[6] Recent Advances in Ni-Catalyzed Asymmetric Reductive Difunctionalization of Alkenes
Ping Yuanyuan
Song Haixia
Kong Wangqing
[J]. CHINESE JOURNAL OF ORGANIC CHEMISTRY, 2022, 42 (10) : 3302 - 3321
[7] Enantioselective Reductive Diarylation of Alkenes by Ni-Catalyzed Domino Heck Cyclization/Cross Coupling
Wang, Kuai
Kong, Wangqing
[J]. SYNLETT, 2019, 30 (09) : 1008 - 1014
[8] Enantioselective Ni-Catalyzed Three-Component Dicarbofunctionalization of Alkenes
Dong, Zhan
Song, Liangliang
Chen, Liang-An
[J]. CHEMCATCHEM, 2023, 15 (18)
[9] Nickel-Catalyzed Enantioselective Reductive Aryl Fluoroalkenylation of Alkenes
Ma, Teng
Chen, Yate
Li, Yuxiu
Ping, Yuanyuan
Kong, Wangqing
[J]. ACS CATALYSIS, 2019, 9 (10): : 9127 - 9133
[10] Ni-Catalyzed Regioselective Reductive 1,3-Dialkenylation of Alkenes
Wickham, Laura M.
Dhungana, Roshan K.
Giri, Ramesh
[J]. ACS OMEGA, 2023, 8 (01): : 1060 - 1066

← 1 2 3 4 5 →