Exo-10,10-diphenyl-2,10-camphanediol as a new chiral auxiliary in asymmetric reduction

Stereoselective reduction of α-keto ester derived from exo-10,10-diphenyl-2,10-camphanediol with various hydrides proceeded with high diastereoselectivities (≥ 96% de) to afford the corresponding α-hydroxy ester with excellent yields. Change of reducing reagents and molar ratio modifications leading...

Full description

Saved in:
Bibliographic Details
Published in:Tetrahedron letters 1999-02, Vol.40 (6), p.1141-1144
Main Authors: Chen, Chiou-Juy, Chu, Ying-Yuan, Liao, Yen-Ying, Tsai, Zong-Hugh, Wang, Chiung-Chiou, Chen, Kwunmin
Format: Article
Language:English
Citations: Items that this one cites
Items that cite this one
Online Access:Get full text
Tags: Add Tag
No Tags, Be the first to tag this record!
Description
Summary:Stereoselective reduction of α-keto ester derived from exo-10,10-diphenyl-2,10-camphanediol with various hydrides proceeded with high diastereoselectivities (≥ 96% de) to afford the corresponding α-hydroxy ester with excellent yields. Change of reducing reagents and molar ratio modifications leading to dramatic changes in diastereofacial selectivity were examined. The auxiliary can be recovered from the asymmetric reaction products without loss of chirality. High optical purity of either of the two diastereomers of α-hydroxyl ester can be prepared from chiral α-keto ester derived from a single enantiomer of exo-10,10-diphenyl-2,10-camphanediol.
ISSN:0040-4039
1873-3581
DOI:10.1016/S0040-4039(98)02548-9