Pyrrolidine-Oxadiazolone Conjugates as Organocatalysts in Asymmetric Michael Reaction

Chandan K. Mahato (TCGLS Member), Sayan Mukherjee, Mrinalkanti Kundu (TCGLS Member), and Animesh Pramanik

The Journal of Organic Chemistry 2019 84 (2), 1053-1063

DOI: 10.1021/acs.joc.8b02393

Abstract

Pyrrolidine-oxadiazolone based organocatalysts are envisaged, synthesized, and utilized for asymmetric Michael reactions. Results of the investigations suggest that some of the catalysts are indeed efficient for stereoselective 1,4-conjugated Michael additions (dr: >97:3, ee up to 99%) in high chemical yields (up to 97%) often in short reaction time. As an extension, one enantiopure Michael adduct has been utilized to synthesize optically active octahydroindole.