Lithium (α-methylbenzyl) allylamide: a differentially protected chiral ammonia equivalent for the asymmetric synthesis of β-amino acids and β-lactams

SG Davies, DR Fenwick

Index: Davies, Stephen G.; Fenwick, David R. Journal of the Chemical Society, Chemical Communications, 1995 , # 11 p. 1109 - 1110

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Abstract

The addition products from the highly stereoselective conjugate additions of lithium (αS)-(α- methylbenzyl) allylamide to α, β-unsaturated tert-butyl esters are efficiently deallylated with tris (triphenylphosphine) rhodium (I) chloride and converted, after transesterification to the methyl esters and cyclisation with methylmagnesium bromide, to the corresponding homochiral N-(α-methylbenzyl)-4-substituted-azetidm-2-ones.