Asymmetric synthesis of allylic secondary alcohols: a new general approach for the preparation of α-amino acids

LJ Drummond, A Sutherland

Index: Drummond, Lorna J.; Sutherland, Andrew Tetrahedron, 2010 , vol. 66, # 29 p. 5349 - 5356

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Citation Number: 15

Abstract

A new general approach for the synthesis of optically active α-amino acids has been developed. The key steps involve a ruthenium catalysed cross-coupling reaction to give a range of α, β-unsaturated ketones, which were then reduced to allylic secondary alcohols in the presence of a chiral CBS oxazaborolidine. A thermal Overman rearrangement was used to prepare a series of allylic trichloroacetimidates and these were converted under ...