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

页码：1023 / 1026

页数：4