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Issue 22, 2001
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Pyrrolidinones derived from (S)-pyroglutamic acid. Part 3. β-Aminopyrrolidinones

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Abstract

The conjugate addition of activated nitrogen nucleophiles, such as hydroxylamine and hydrazine derivatives, to α,β-unsaturated bicyclic lactam 1a gave the corresponding β-amino products 9a–g in good yield and excellent diastereoselectivity. These products can be manipulated to afford enantiopure β-aminopyrrolidinones of potential application as conformationally-constrained, substituted glutamate templates of well-defined stereochemistry.

Graphical abstract: Pyrrolidinones derived from (S)-pyroglutamic acid. Part 3. β-Aminopyrrolidinones

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Publication details

The article was received on 26 Jul 2001, accepted on 19 Sep 2001 and first published on 25 Oct 2001


Article type: Paper
DOI: 10.1039/B106782F
J. Chem. Soc., Perkin Trans. 1, 2001, 2997-3006

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    Pyrrolidinones derived from (S)-pyroglutamic acid. Part 3. β-Aminopyrrolidinones

    P. W. H. Chan, I. F. Cottrell and M. G. Moloney, J. Chem. Soc., Perkin Trans. 1, 2001, 2997
    DOI: 10.1039/B106782F

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