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Pyrrolidinones derived from (S)-pyroglutamic acid: penmacric acid and analogues
Muhammed Anwar1, Jonathan H Bailey, Laura C Dickinson
1Department of Chemistry, Dyson Perrins Laboratory, The University of Oxford, South Parks Road, Oxford, OX1 3QY.
Organic & Biomolecular Chemistry
|August 30, 2003
Abstract:
Alkylation reactions using alpha-halolactams or lactam enolates derived from bicyclic lactam templates can proceed with high endo- or exo- diastereoselectivity respectively. In the latter case, stereochemical correction by means of enolate generation and hindered phenol quench is possible with moderate efficiency. This protocol has been applied to the synthesis of protected penmacric acid and its analogues.