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

[31] Ni-Catalyzed Reductive Homocoupling of Unactivated Alkyl Bromides at Room Temperature and Its Synthetic Application [J].

Peng, Yu ;

Luo, Long ;

Yan, Chang-Song ;

Zhang, Jian-Jian ;

Wang, Ya-Wen .

JOURNAL OF ORGANIC CHEMISTRY, 2013, 78 (21) :10960-10967

[32] Ni-Catalyzed Aryl Thioester Synthesis via Thioester Transfer Reaction [J].

Liang, Luqi ;

Xi, Juan ;

Jiang, Ruonan ;

Yang, Yi ;

Sun, Fenggang ;

Zhang, Lizhi ;

Li, Xinjin ;

Liu, Hui .

CHINESE JOURNAL OF ORGANIC CHEMISTRY, 2023, 43 (04) :1566-1573

[33] Ni-Catalyzed Reductive 1,2-Cross-Dialkylation of Unactivated Alkenes with Two Alkyl Bromides [J].

Zhang, Jian-Xin ;

Shu, Wei .

ORGANIC LETTERS, 2022, 24 (21) :3844-3849

[34] Ni-catalyzed enantioconvergent deoxygenative reductive cross-coupling of unactivated alkyl alcohols and aryl bromides [J].

Zhang, Li-Li ;

Gao, Yu-Zhong ;

Cai, Sheng-Han ;

Yu, Hui ;

Shen, Shou-Jie ;

Ping, Qian ;

Yang, Ze-Peng .

NATURE COMMUNICATIONS, 2024, 15 (01)

[35] Ni-Catalyzed Cross-Coupling of Dimethyl Aryl Amines with Arylboronic Esters under Reductive Conditions [J].

Cao, Zhi-Chao ;

Xie, Si-Jun ;

Fang, Huayi ;

Shi, Zhang-Jie .

JOURNAL OF THE AMERICAN CHEMICAL SOCIETY, 2018, 140 (42) :13575-13579

[36] Light-Promoted Ni-Catalyzed Cross-Coupling of Aryl Chlorides with Hydrazides: Application to the Synthesis of Rizatriptan [J].

Li, Fei ;

Xiong, Weikang ;

Song, Geyang ;

Yan, Yonggang ;

Li, Gang ;

Wang, Chao ;

Xiao, Jianliang ;

Xue, Dong .

ORGANIC LETTERS, 2023, 25 (18) :3287-3292

[37] Synthesis of trifluoromethylated thioethers via Ni-catalyzed reductive C-S coupling [J].

Liu, Wei ;

He, Yan ;

Liu, Zhi-Yuan ;

Li, Yanlin ;

Li, Yan ;

Wu, Bing-Bing ;

Jin, Ruo-Xin ;

Wang, Xi-Sheng .

ORGANIC CHEMISTRY FRONTIERS, 2023, 10 (12) :2943-2948

[38] Alkenylation and Arylation of Peptides via Ni-Catalyzed Reductive Coupling of α-C-Tosyl Peptides with Csp2 Triflates/Halides [J].

Tao, Xianghua ;

Ma, Guobin ;

Song, Yanhong ;

Chen, Yunrong ;

Qian, Qun ;

Sun, Deli ;

Gong, Hegui .

ORGANIC LETTERS, 2021, 23 (19) :7418-7422

[39] Ni-Catalyzed Enantioselective Reductive Cyclization/Amidation and Amination of 1,6-Enynes and 1,7-Enynes [J].

Hu, Shengwei ;

Wang, Xiaoqin ;

Wu, Tianbao ;

Ding, Zhengtian ;

Wang, Minyan ;

Kong, Wangqing .

ANGEWANDTE CHEMIE-INTERNATIONAL EDITION, 2025, 64 (01)

[40] Ni-catalyzed highly enantioselective synthesis of sulfur protected P-stereogenic supramolecular phosphine [J].

Koshti, Vijay S. ;

Chandanshive, Amol C. ;

Mote, Nilesh R. ;

Chikkali, Samir H. .

JOURNAL OF CHEMICAL SCIENCES, 2021, 133 (04)

← 1 2 3 4 5 →