ePrints@IIScePrints@IISc Home | About | Browse | Latest Additions | Advanced Search | Contact | Help

Ring-Opening 1,3-Carbothiolation of Donor-Acceptor Cyclopropanes Using Alkyl Halides and in Situ Generated Dithiocarbamates

Guin, A and Deswal, S and Biju, AT (2022) Ring-Opening 1,3-Carbothiolation of Donor-Acceptor Cyclopropanes Using Alkyl Halides and in Situ Generated Dithiocarbamates. In: Journal of Organic Chemistry, 87 (9). pp. 6504-6513.

[img] PDF
jou_org_che_87-9_6504-6513_2022.pdf - Published Version
Restricted to Registered users only

Download (1MB) | Request a copy
Official URL: https://doi.org/10.1021/acs.joc.2c00447

Abstract

Two-step, ring-opening 1,3-carbothiolation of donor-acceptor (D-A) cyclopropanes employing alkyl halides and in situ generated dithiocarbamates (from amines and CS2) has been demonstrated under mild conditions. The reaction is operationally simple and works with good functional group compatibility. Three new bonds including C-N, C-S, and C-C are formed in this 1,3-bifunctionalization strategy. Electron-poor olefins can also be used as electrophiles instead of alkyl halides. The use of enantiomerically pure D-A cyclopropane afforded enantiopure 1,3-carbothiolated product, thus demonstrating the stereospecificity of the reaction. © 2022 American Chemical Society. All rights reserved.

Item Type: Journal Article
Publication: Journal of Organic Chemistry
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: 19 May 2022 08:55
Last Modified: 19 May 2022 08:55
URI: https://eprints.iisc.ac.in/id/eprint/72055

Actions (login required)

View Item View Item