Tetrahedron: Asymmetry

Asymmetric synthesis of R-β-amino butanoic acid and S-β-tyrosine: Homochiral lithium amide equivalents for Michael additions to α, β-unsaturated esters.

SG Davies, O Ichihara

Index: Davies, Stephen G.; Ichihara, Osamu Tetrahedron: Asymmetry, 1991 , vol. 2, # 3 p. 183 - 186

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Citation Number: 305

Abstract

Abstract Michael addition of the lithium amide derived from RN-(α-methylbenzyl) benzylamine to benzyl E-crotonate is highly stereoselective (95% de) giving after debenzylation and crystallisation homochiral R-β-amino butanoic acid. A similar addition to methyl E-(p-benzyloxy) cinnamate is completely stereoselective giving after debenzylation and acid hydrolysis homochiral S-β-tyrosine as its HCl salt.