Homochiral lithium amides for the asymmetric synthesis of β-amino acids

…, NM Garrido, D Kruchinin, O Ichihara, LJ Kotchie…

Index: Davies, Stephen G.; Garrido, Narciso M.; Kruchinin, Dennis; Ichihara, Osamu; Kotchie, Luke J.; Price, Paul D.; Mortimer, Anne J. Price; Russell, Angela J.; Smith, Andrew D. Tetrahedron Asymmetry, 2006 , vol. 17, # 12 p. 1793 - 1811

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Citation Number: 71

Abstract

Secondary homochiral lithium amides derived from α-methylbenzylamine undergo highly diastereoselective conjugate additions to a range of α, β-unsaturated esters. The corresponding β-amino acids are readily liberated by successive N-debenzylation and ester hydrolysis, furnishing (R)-β-amino butyric acid,(R)-β-amino pentanoic acid,(S)-β-leucine,(R)- β-amino octanoic acid,(S)-β-phenylalanine,(S)-β-tyrosine methyl ether,(S)-β-tyrosine ...