Catalytic Asymmetric [4+1] Annulation of Sulfur Ylides with Copper-Allenylidene Intermediates

被引：235

作者：

Wang, Qiang ^{[1
]}

Li, Tian-Ren ^{[1
]}

Lu, Liang-Qiu ^{[1
]}

Li, Miao-Miao ^{[1
]}

Zhang, Kai ^{[1
]}

Xiao, Wen-Jing ^{[1
,2
]}

机构：

[1] Cent China Normal Univ, Coll Chem, 152 Luoyu Rd, Wuhan 430079, Hubei, Peoples R China

[2] Lanzhou Univ, State Key Lab Appl Organ Chem, Lanzhou 730000, Gansu, Peoples R China

来源：

JOURNAL OF THE AMERICAN CHEMICAL SOCIETY | 2016年 / 138卷 / 27期

基金：

中国国家自然科学基金;

关键词：

PROPARGYLIC SUBSTITUTION-REACTIONS; 3+2 CYCLOADDITION; CASCADE REACTIONS; ENANTIOSELECTIVE SYNTHESIS; BETA-KETOESTERS; ALCOHOLS; INDOLES; ALKYLATION; ESTERS; CYCLOPROPANATION;

D O I：

10.1021/jacs.6b04414

中图分类号：

O6 [化学];

学科分类号：

0703 ;

摘要：

The first copper-catalyzed asymmetric decarboxylative [4 + 1] cycloaddition of propargylic carbamates and sulfur ylides was successfully developed. This strategy led to a series of chiral indolines with synthetically flexible alkyne groups in good yields and with high enantio- and diastereoselectivities (up to 99% yield, 98% ee, and >95:5 dr). A possible mechanism and stereoinduction mode with copper-allenylidenes were proposed as the possible dipolar intermediate.

引用

页码：8360 / 8363

页数：4

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