Extending Pummerer reaction chemistry. Asymmetric synthesis of spirocyclic oxindoles via chiral indole-2-sulfoxides

被引：56

作者：

Feldman, Ken S. ^{[1
]}

Karatjas, Andrew G. ^{[1
]}

机构：

[1] Penn State Univ, Dept Chem, University Pk, PA 16802 USA

来源：

ORGANIC LETTERS | 2006年 / 8卷 / 18期

关键词：

D O I：

10.1021/ol0617244

中图分类号：

O62 [有机化学];

学科分类号：

070303 ; 081704 ;

摘要：

The conversion of (S-s)-3-(omega-allylsilane and silyl enol ether)indole-2-sulfoxides to spirocyclic indolenines and then to oxindoles proceeds, in favorable cases, with moderate levels of chirality transfer from sulfur to C(3) of the indole core. A mechanistic model, which features either an Sn2'-like additive Pummerer sequence or a tight ion pair generated by an Sn1-like vinylogous Pummerer transform, is proposed to rationalize the sense of asymmetric induction.

引用

页码：4137 / 4140

页数：4

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