Tetrahedron: Asymmetry

On the origins of enantioselectivity in oxazaborolidine mediated carbonyl reductions

GB Jones, SB Heaton, BJ Chapman, M Guzel

Index: Jones, Graham B.; Heaton, Steven B.; Chapman, Brant J.; Guzel, Mustafa Tetrahedron Asymmetry, 1997 , vol. 8, # 21 p. 3625 - 3636

Full Text: HTML

Citation Number: 47

Abstract

A series of tricyclic oxazaborolidine catalysts have been prepared from readily available (S)- indoline-2-carboxylic acid. In each case, an arene chromium (0) carbonyl group was introduced on one face of the catalyst. Results obtained in the borane mediated reduction of ketones highlight the stereodirective importance of the α, α-appendages in the catalyst architecture.