Kinetic resolution of amines: A highly enantioselective and chemoselective acetylating agent with a unique solvent-induced reversal of stereoselectivity

被引：95
作者：
Arseniyadis, S
Valleix, A
Wagner, A
Mioskowski, C
机构：
[1] Fac Pharm, CNR, Lab Synth Bioorgan, UMR 7514, F-67400 Illkirch Graffenstaden, France
[2] CEA Saclay, Serv Mol Marquees, F-91191 Gif Sur Yvette, France
来源：
ANGEWANDTE CHEMIE-INTERNATIONAL EDITION | 2004年 / 43卷 / 25期
关键词：
acylation; enantioselectivity; kinetic resolution; solvent effects;
D O I：
10.1002/anie.200453956
中图分类号：
O6 [化学];
学科分类号：
0703 ;
摘要：
Solvents lend a hand: Changing the polarity of the reaction solvent from 1,3-dimethyltetrahydropyrimidin-2-one (DMPU) to toluene reverses the stereo-selectivity observed in the acetylation of amines with (1S,2S)-1 (see scheme). Optimizing the reaction conditions led to an unprecedented 90% ee (S) in DMPU at -20°C with a 33% conversion.
引用
收藏
页码：3314 / 3317
页数：4
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