Lewis acid-catalyzed one-pot thioalkenylation of donor-acceptor cyclopropanes using in situ generated dithiocarbamates and propiolates

Harikumar, S and Kandy, LTK and Guin, A and Biju, AT (2024) Lewis acid-catalyzed one-pot thioalkenylation of donor-acceptor cyclopropanes using in situ generated dithiocarbamates and propiolates. In: Organic and Biomolecular Chemistry, 22 (9). pp. 1834-1838.

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Abstract

Lewis acid-catalyzed one-pot 1,3-thioalkenylation of donor-acceptor (D-A) cyclopropanes has been demonstrated employing in situ generated dithiocarbamates (from amines and CS2) as nucleophilic triggers and alkyl propiolates as electrophiles. This method addresses the limitations of previously known carbothiolation approach, eliminating the need for extra filtration prior to the subsequent trapping with electrophiles. The anticipated thioalkenylated products were obtained in good to excellent yields with a moderate to good E/Z ratio. Three new bonds (C-N, C-S, and C-C) are formed during this 1,3-bisfunctionalization reaction. Notably, employing enantiomerically pure D-A cyclopropanes resulted in enantiopure 1,3-thioalkenylated products, underscoring the stereospecific nature of the developed reaction. © 2024 The Royal Society of Chemistry.

Item Type:	Journal Article
Publication:	Organic and Biomolecular Chemistry
Publisher:	Royal Society of Chemistry
Additional Information:	The copyright for this article belongs to the Royal Society of Chemistry.
Keywords:	Catalysis; Propane, Dithiocarbamates; Donor-acceptor cyclopropanes; Electrophiles; Enantiopure; Lewis Acid; One pot; Stereospecific; Z ratio, Amines, amine; cyclopropane derivative; dithiocarbamic acid; electrophile; Lewis acid, article; catalysis; drug analysis; filtration; nucleophilicity
Department/Centre:	Division of Chemical Sciences > Organic Chemistry
Date Deposited:	08 Apr 2024 09:11
Last Modified:	08 Apr 2024 09:11
URI:	https://eprints.iisc.ac.in/id/eprint/84695

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