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

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.