Asymmetric Trisubstituted Aziridination of Aldimines and Ketimines using N-α-Diazoacyl Camphorsultams

被引:24
作者
Hashimoto, Takuya [1 ]
Nakatsu, Hiroki [1 ]
Yamamoto, Kumiko [1 ]
Watanabe, Shogo [1 ]
Maruoka, Keiji [1 ]
机构
[1] Kyoto Univ, Grad Sch Sci, Dept Chem, Sakyo Ku, Kyoto 6068502, Japan
关键词
asymmetric synthesis; aziridine; camphorsultam; chiral auxiliaries; diazo compounds; CARBON QUATERNARY CENTER; AMINO-ACIDS; STEREOSELECTIVE-SYNTHESIS; ENANTIOSELECTIVE SYNTHESIS; CATALYTIC AZIRIDINATION; MANNICH REACTIONS; LEWIS-ACID; CONSTRUCTION; IMINES; VAPOL;
D O I
10.1002/asia.201000604
中图分类号
O6 [化学];
学科分类号
0703 ;
摘要
The acid-catalyzed reaction of diazoacetates and aldimines (Brookhart-Templeton aziridination) is now recognized as a reliable method to provide enantiomerically enriched disubstituted aziridines, thus owing to the development of asymmetric catalysis. However, the extension of this method to prepare trisubstituted aziridines has not been explored to date, even for racemic products. In this context, and considering their synthetic importance and lack of alternative direct synthetic methods, we recently launched a program to realize this unmet challenge. Herein, we report a detailed study, which led to the establishment of a highly stereoselective synthesis for various trisubstituted aziridines, building on the use of N-alpha-diazoacyl camphorsultams as a key component.
引用
收藏
页码:607 / 613
页数:7
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