Pyrrolidinones derived from (S)-pyroglutamic acid. Part 3. beta-aminopyrrolidinones

The conjugate addition of activated nitrogen nucleophiles, such as hydroxylamine and hydrazine derivatives, to, unsaturated bicyclic lactam 1a gave the corresponding beta -amino products 9a-g in good yield and excellent diastereoselectivity. These products can be manipulated to a ord enantiopure bet...

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Bibliographic Details
Published inPerkin 1 : an international journal of organic and bio-organic chemistry no. 22; pp. 2997 - 3006
Main Authors Chan, PWH, Cottrell, IF, Moloney, MG
Format Journal Article
LanguageEnglish
Published CAMBRIDGE Royal Soc Chemistry 15.11.2001
Subjects
Chemistry
Chemistry, Organic
Physical Sciences
Science & Technology
MECHANISM
ANALOGS
CHIRAL BICYCLIC LACTAMS
ESTERS
ASYMMETRIC CONJUGATE ADDITIONS
ALPHA-AMINO-ACIDS
DERIVATIVES
STEREOSELECTIVE SYNTHESIS
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Summary:The conjugate addition of activated nitrogen nucleophiles, such as hydroxylamine and hydrazine derivatives, to, unsaturated bicyclic lactam 1a gave the corresponding beta -amino products 9a-g in good yield and excellent diastereoselectivity. These products can be manipulated to a ord enantiopure beta -aminopyrrolidinones of potential application as conformationally-constrained, substituted glutamate templates of well-defined stereochemistry.
ISSN:1472-7781
DOI:10.1039/b106782f