ChemInform Abstract: 4‐Benzyl‐2,3‐didehydroprolinate (IV) as a Homochiral Template for Michael Additions. Synthesis of Enantiopure α‐Allokainoids (VII), β‐Kainoids (XX), 2,3‐Methanoprolines (XVI) and Other 3,4 Disubstituted Prolines (XIII).

Abstract

1997 stereochemistry stereochemistry (general, optical resolution) O 0030 03 -060 4-Benzyl-2,3-didehydroprolinate (IV) as a Homochiral Template for Michael Additions. Synthesis of Enantiopure α-Allokainoids (VII), β-Kainoids (XX), 2,3-Methanoprolines (XVI) and Other 3,4 Disubstituted Prolines (XIII). -Compound (IV) undergoes Michael additions with stabilized carbanions and cuprates to give exclusively the enantiopure all-trans 3,4-disubstituted prolinates. The high stereoselectivity observed is caused by the C-4 substituent of the Michael acceptor. -(EZQUERRA, J.; ESCRIBANO, A.; RUBIO, A.; REMUINAN, M. J.; VAQUERO, J.