Highly diastereo- and enantioselective construction of a spiro[cyclopenta[b]indole-1,3′-oxindole] scaffold via catalytic asymmetric formal [3+2] cycloadditions

被引：147

作者：

Tan, Wei ^{[1
]}

Li, Xin ^{[1
]}

Gong, Yu-Xin ^{[1
]}

Ge, Meng-Di ^{[1
]}

Shi, Feng ^{[1
]}

机构：

[1] Jiangsu Normal Univ, Sch Chem & Chem Engn, Xuzhou 221116, Peoples R China

来源：

CHEMICAL COMMUNICATIONS | 2014年 / 50卷 / 100期

关键词：

BRONSTED-ACID; 1,3-DIPOLAR CYCLOADDITIONS; AZOMETHINE YLIDES; ALKYLATION; INHIBITORS; ALDEHYDES; 3-INDOLYLMETHANOLS; HETEROCYCLES; ALCOHOLS;

D O I：

10.1039/c4cc07246d

中图分类号：

O6 [化学];

学科分类号：

0703 ;

摘要：

An organocatalytic asymmetric formal [3+2] cycloaddition of isatin-derived 3-indolylmethanol with 3-methyl-2-vinylindole has been established, leading to highly stereoselective construction of a spiro[cyclopenta[b]indole-1,3 '-oxindole] scaffold with the concomitant creation of three contiguous stereogenic centers (72-99% yield, all > 95 : 5 dr, 90-98% ee), one of which is an all-carbon quaternary stereogenic center.

引用

页码：15901 / 15904

页数：4

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