Catalytic Asymmetric 6π Electrocyclization: Enantioselective Synthesis of Functionalized Indolines

被引：49

作者：

Maciver, Eleanor E. ^{[1
]}

Thompson, Sam ^{[1
]}

Smith, Martin D. ^{[1
]}

机构：

[1] Univ Oxford, Chem Res Lab, Oxford OX1 3TA, England

来源：

ANGEWANDTE CHEMIE-INTERNATIONAL EDITION | 2009年 / 48卷 / 52期

基金：

英国工程与自然科学研究理事会;

关键词：

asymmetric catalysis; electrocyclization; organocatalysis; phase transfer; torquoselectivity; MANNICH-TYPE REACTION; X=Y-ZH SYSTEMS; STEREOSELECTIVE-SYNTHESIS; LEWIS-ACID; POTENTIAL 1,3-DIPOLES; NAZAROV CYCLIZATION; RING-CLOSURE; 1,5-ELECTROCYCLIZATION; CYCLOHEXENONES; DERIVATIVES;

D O I：

10.1002/anie.200905169

中图分类号：

O6 [化学];

学科分类号：

0703 ;

摘要：

(figure represented) How to close a ring: An approach to catalytic asymmetric 6π electrocyclization leads to a highly enantioselective process that was used in the synthesis of chiral indolines (see scheme). Treatment of N-aryl imines under phase transfer conditions in the presence of N-benzyl cinchonidinium chloride generates a delocalized 2-aza-pentadienyl anion system that cyclizes in up to 99% yield and 98% ee. © 2009 Wiley-VCH Verlag GmbH & Co. KGaA.

引用

页码：9979 / 9982

页数：4

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