Organocatalytic Activation of the Leaving Group in the Intramolecular Asymmetric SN2′ Reaction

被引：28

作者：

Kuroda, Yusuke ^{[1
]}

Harada, Shingo ^{[1
]}

Oonishi, Akinori ^{[1
]}

Yamaoka, Yousuke ^{[1
]}

Yamada, Ken-ichi ^{[1
]}

Takasu, Kiyosei ^{[1
]}

机构：

[1] Kyoto Univ, Grad Sch Pharmaceut Sci, Sakyo Ku, Kyoto 6068501, Japan

来源：

ANGEWANDTE CHEMIE-INTERNATIONAL EDITION | 2015年 / 54卷 / 28期

关键词：

asymmetric catalysis; nucleophilic substitution; organocatalysis; pyrrolidines; ACID-CATALYZED DESYMMETRIZATION; CHIRAL PHOSPHORIC-ACIDS; BOND-FORMING REACTIONS; BRONSTED ACID; ENANTIOSELECTIVE SYNTHESIS; ALLYLIC ALKYLATION; EPISULFONIUM IONS; MESO-AZIRIDINES; PRENYLTRANSFERASES; NUCLEOPHILES;

D O I：

10.1002/anie.201502831

中图分类号：

O6 [化学];

学科分类号：

0703 ;

摘要：

A BrOnsted-acid-catalyzed intramolecular enantioselective S(N)2 reaction was developed utilizing trichloroacetimidate as a leaving group. The findings indicated that dual activation of the substrates is operative. This metal-free allylic alkylation allows highly enantioselective access to 2-vinylpyrrolidines bearing various substituents.

引用

页码：8263 / 8266

页数：4

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