Enantioselective ring opening of meso-epoxides by aromatic amines catalyzed by lanthanide iodo binaphtholates

被引：112
|
作者：
Carrée, F [1 ]
Gil, R [1 ]
Collin, J [1 ]
机构：
[1] Univ Paris 11, ICMMO, UMR 8075, Lab Catalyse Mol, F-91405 Orsay, France
来源：
ORGANIC LETTERS | 2005年 / 7卷 / 06期
关键词：
D O I：
10.1021/ol0475360
中图分类号：
O62 [有机化学];
学科分类号：
070303 ; 081704 ;
摘要：
Lanthanide iodo binaphtholates are efficient enantioselective catalysts for the ring opening of meso-epoxides by various aromatic amines. The study of the influence of temperature on the ring opening of cyclohexene oxide by o-anisidine catalyzed by the samarium complex shows an isoinversion effect with the maximum enantiomeric excess at -40 C. Reactions of aniline, o-anisidine, or p=anisidine with five- or six-membered ring epoxides at this temperature allow the preparation of beta-amino alcohols with enantiomeric excesses up to 93%.
引用
收藏
页码：1023 / 1026
页数：4
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