Affordable Access

Publisher Website

Stereoselective reduction of ketones by histidine-alkoxysilane complexes: The role of imidazole in nucleophilic substitution at silicon

Authors
Journal
Tetrahedron Letters
0040-4039
Publisher
Elsevier
Publication Date
Volume
40
Issue
18
Identifiers
DOI: 10.1016/s0040-4039(99)00543-2

Abstract

Abstract The reduction of carbonyl compounds with transient, hypervalent silicon hydrides is described. Trialkoxysilanes, upon activation by a catalytic amount of lithium imidazolide or the mono or dilithium salt of histidine, but not by neutral imidazole or histidine, reduced the carbonyl groups of various ketones. Enantiomerically enriched product alcohols were recovered in good to excellent yield (70 – 95%) with e.e.'s ranging from 5–75% when catalyzed by histidine derivatives.

There are no comments yet on this publication. Be the first to share your thoughts.