NHC-Catalyzed 3+3] Annulation of Thioamides and Modified Enals for the Enantioselective Synthesis of Functionalized Thiazinones

Ghosh, Arghya and Barik, Soumen and Biju, Akkattu T (2019) NHC-Catalyzed 3+3] Annulation of Thioamides and Modified Enals for the Enantioselective Synthesis of Functionalized Thiazinones. In: ORGANIC LETTERS, 21 (21). pp. 8598-8602.

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Abstract

N-Heterocyclic carbene (NHC)-catalyzed 3 + 3] annulation of thioamides with modified enals allowing the enantioselective synthesis of functionalized 1,3-thiazin-4-ones is reported. The NHC generated from the chiral triazolium salt was optimal and the reaction is initiated by the thia-Michael addition to catalytically generated alpha,beta-unsaturated acylazolium intermediates derived from 2-bromoenals, followed by intramolecular cyclization. This operationally simple procedure offers a straightforward and rapid access to target compounds in moderate to good yields and enantiomeric ratio values.

Item Type:	Journal Article
Publication:	ORGANIC LETTERS
Publisher:	AMER CHEMICAL SOC
Additional Information:	Copyright of this article belongs to AMER CHEMICAL SOC
Keywords:	N-HETEROCYCLIC CARBENES; ACYL; CONSTRUCTION; MECHANISM; UMPOLUNG
Department/Centre:	Division of Chemical Sciences > Organic Chemistry
Date Deposited:	17 Dec 2019 09:32
Last Modified:	17 Dec 2019 09:32
URI:	http://eprints.iisc.ac.in/id/eprint/63943

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