Kinetic Resolution Approach to the Synthesis of C-N Axially Chiral N-Aryl Aminomaleimides via NHC-Catalyzed [3 + 3] Annulation

Barik, S and Das, RC and Balanna, K and Biju, AT (2022) Kinetic Resolution Approach to the Synthesis of C-N Axially Chiral N-Aryl Aminomaleimides via NHC-Catalyzed [3 + 3] Annulation. In: Organic Letters, 24 (29). pp. 5456-5461.

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Abstract

Chiral NHC-catalyzed kinetic resolution of N-aryl aminomaleimides allowing the synthesis of C-N axially chiral N-aryl aminomaleimides via remote chirality control is presented. The catalytically generated α,β-unsaturated acylazoliums from 2-bromoenals underwent selective 3 + 3 annulation with one of the enantiomers of maleimide to furnish fused-dihydropyridinone (bearing axial/central chirality, up to 6:1 dr, >99:1 er) leaving the enantioenriched opposite enantiomer (up to >99:1 er). Studies on C-N bond rotation barrier and dependence on temperature are also provided. © 2022 American Chemical Society. All rights reserved.

Item Type:	Journal Article
Publication:	Organic Letters
Publisher:	American Chemical Society
Additional Information:	The copyright for this article belongs to the American Chemical Society.
Department/Centre:	Division of Chemical Sciences > Organic Chemistry
Date Deposited:	06 Oct 2022 10:45
Last Modified:	06 Oct 2022 10:45
URI:	https://eprints.iisc.ac.in/id/eprint/77201

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