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
收藏
页码：8263 / 8266
页数：4
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