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Issue 21, 1999
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Asymmetric synthesis of β-lactams and pseudopeptides via stereoselective conjugate additions of lithium (α-methylbenzyl)allylamide to α,β-unsaturated iron acyl complexes

Abstract

Lithium (α-methylbenzyl)allylamide 2 undergoes stereoselective conjugate additions to α,β-unsaturated iron acyl complexes 3a–c to afford β-amino iron acyl adducts 5a–c and 6a–c. These adducts may be deallylated smoothly using palladium(0) catalysis providing the corresponding homochiral secondary amines 7a–c which, upon oxidative decomplexation with bromine or N-bromosuccinimide, undergo direct β-lactam ring formation. The diastereoselectivity for the conjugate addition to 3a may be further improved by the use of magnesium amide 10. Oxidative decomplexation of one of the β-amino iron acyl adducts 5b in the presence of α-amino esters provides pseudopeptide fragments comprising an α-amino acid coupled to a β-amino acid.

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Article type: Paper
DOI: 10.1039/A906633K
Citation: J. Chem. Soc., Perkin Trans. 1, 1999,0, 3105-3110
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    Asymmetric synthesis of β-lactams and pseudopeptides via stereoselective conjugate additions of lithium (α-methylbenzyl)allylamide to α,β-unsaturated iron acyl complexes

    S. G. Davies, N. M. Garrido, P. A. McGee and J. P. Shilvock, J. Chem. Soc., Perkin Trans. 1, 1999, 0, 3105
    DOI: 10.1039/A906633K

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