Enantioselective diethylzinc addition to aromatic and aliphatic aldehydes using (3R,5R)-dihydroxypiperidine derivatives catalyst

被引：62
|
作者：
Roudeau, R [1 ]
Pardo, DG [1 ]
Cossy, J [1 ]
机构：
[1] Ecole Super Phys & Chim Ind Ville Paris, Chim Organ Lab, CNRS, F-75231 Paris 05, France
来源：
TETRAHEDRON | 2006年 / 62卷 / 10期
关键词：
enantioselective addition; aliphatic aldehydes; chiral ligands;
D O I：
10.1016/j.tet.2005.11.070
中图分类号：
O62 [有机化学];
学科分类号：
070303 ; 081704 ;
摘要：
A series of chiral (3R,5R)-dihydroxypiperidine derivatives 3a-f were conveniently prepared from trans-4-hydroxy-L-proline and applied to the catalytic enantioselective addition of diethylzinc to benzaldehyde and heptanal. Among them, 3d was found to show the best asymmetric induction in promoting the addition of Et2Zn to various aldehydes, providing (R)-secondary alcohols in up to 98% ee. (c) 2005 Elsevier Ltd. All rights reserved.
引用
收藏
页码：2388 / 2394
页数：7
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