Synthesis and Use of α-Silyl-Substituted α-Hydroxyacetic Acids

C Bolm, A Kasyan, P Heider, S Saladin, K Drauz…

Index: Bolm, Carsten; Kasyan, Andrey; Heider, Peter; Saladin, Sandra; Drauz, Karlheinz; Guenther, Kurt; Wagner, Christoph Organic Letters, 2002 , vol. 4, # 13 p. 2265 - 2267

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Citation Number: 32

Abstract

Rhodium-catalyzed oxygen transfer was used to generate benzyl 2-silyl-2-oxoacetates in good yields. The hydrogenation of these compounds led to chiral α-silyl-substituted α- hydroxyacetic acids. Resolution by means of HPLC using a chiral stationary phase afforded an enantiomerically pure representative of this class of compounds, which was successfully applied as a chiral ligand in an asymmetric aldol-type reaction.