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J Org Chem. 2019 Jan 18;84(2):1053-1063. doi: 10.1021/acs.joc.8b02393. Epub 2019 Jan 03.

Pyrrolidine-Oxadiazolone Conjugates as Organocatalysts in Asymmetric Michael Reaction.

The Journal of organic chemistry

Chandan K Mahato, Sayan Mukherjee, Mrinalkanti Kundu, Animesh Pramanik

Affiliations

  1. TCG Lifesciences Pvt. Ltd. , BN-7 , Salt Lake City, Kolkata 700091 , India.
  2. Department of Chemistry , University of Calcutta , 92, A. P. C. Road , Kolkata 700009 , India.

PMID: 30577689 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.

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