Enantioselective Synthesis of Dihydrothiopyranones via NHC-Catalyzed 3 + 3 Annulation of 2-Bromoenals with β-Oxodithioesters

Barik, S and Shee, S and Gonnade, RG and Biju, AT (2022) Enantioselective Synthesis of Dihydrothiopyranones via NHC-Catalyzed 3 + 3 Annulation of 2-Bromoenals with β-Oxodithioesters. In: Organic Letters, 24 (48). pp. 8848-8853.

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Abstract

The N-heterocyclic carbene (NHC)-organocatalyzed 3 + 3 annulation of 2-bromoenals with β-oxodithioesters resulting in the enantioselective synthesis of dihydrothiopyranones is presented. The chiral α,β-unsaturated acylazoliums generated from 2-bromoenals and carbenes underwent smooth interception with the sulfur nucleophiles to furnish the sulfur heterocycles in satisfactory yields/selectivity. The regioselective formation of dihydrothiopyranones over the competing dihydropyranones is noteworthy. © 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 American Chemical Society
Department/Centre:	Division of Chemical Sciences > Organic Chemistry
Date Deposited:	13 Jan 2023 11:51
Last Modified:	13 Jan 2023 11:51
URI:	https://eprints.iisc.ac.in/id/eprint/79148

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