180334-91-2Relevant academic research and scientific papers
Pyrrolidinones derived from (S)-pyroglutamic acid. Part 1. Conformationally constrained glutamate
Bailey, Jonathan H.,Cherry, David T.,Dyer, James,Moloney, Mark G.,Bamford, Mark J.,Keeling, Steve,Lament, R. Brian
, p. 2783 - 2792 (2000)
Novel conformationally constrained pyroglutaminols and pyroglutamates are readily available using an α,β-unsaturated bicyclic lactam as a template for diastereocontrolled enolate additions in the key step; zinc enolates are particularly effective in this regard. The bicyclic ring system both controls and permits the determination of ring stereochemistry. The utility of this methodology is demonstrated by a formal total synthesis of the NMDA receptor agonist, CPAA 11. The Royal Society of Chemistry 2000.
Functionalised pyrrolidinones by conjugate addition of stabilised enolates and Reformatsky reagents
Dyer, James,Keeling, Steve,Moloney, Mark G.
, p. 4573 - 4576 (1996)
The α,β-unsaturated lactam 1b has been found to readily undergo conjugate addition reactions with a range of stabilised carbon nucleophiles and Reformatsky reagents under mild conditions in good yield with high diastereoselectivity. This method provides a simple and versatile approach to highly functionalised pyrrolidinones.
