Enantioselective reduction of α-substituted ketones mediated by the boronate ester TarB-NO 2

…, N Ball-Jones, D Haddenham, J Saavedra, C DeLieto…

Index: Eagon, Scott; Ball-Jones, Nicholas; Haddenham, Dustin; Saavedra, Jaime; Delieto, Cassandra; Buckman, Matthew; Singaram, Bakthan Tetrahedron Letters, 2010 , vol. 51, # 49 p. 6418 - 6421

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Citation Number: 14

Abstract

A facile and mild reduction procedure is reported for the preparation of chiral secondary alcohols prepared from α-substituted ketones using sodium borohydride and the chiral boronate ester (l)-TarB-NO2. Direct reduction of substituted ketones bearing Lewis basic heteroatoms generally provided secondary alcohols of only modest enantiomeric excess likely due to either competition between the target carbonyl and the functionalized ...