Tetrahedron

Double asymmetric induction as a mechanistic probe: the doubly diastereoselective conjugate addition of enantiopure lithium amides to enantiopure α, β-unsaturated …

SG Davies, JA Lee, PM Roberts, JE Thomson, J Yin

Index: Davies, Stephen G.; Lee, James A.; Roberts, Paul M.; Thomson, James E.; Yin, Jingda Tetrahedron, 2011 , vol. 67, # 34 p. 6382 - 6403

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Citation Number: 18

Abstract

The doubly diastereoselective conjugate addition of the antipodes of lithium N-benzyl-N-(α- methylbenzyl) amide to a range of enantiopure α, β-unsaturated esters [derived from Corey's 8-phenylmenthol chiral auxiliary] and enantiopure α, β-unsaturated hydroxamates [derived from our 'chiral Weinreb amide'auxiliary (S)-N-1-(1′-naphthyl) ethyl-O-tert- butylhydroxylamine] has been used as a mechanistic probe to determine the reactive ...