Catalytic Enantioselective Synthesis of 3,4-Unsubstituted Thiochromenes through Sulfa-Michael/Julia Kocienski Olefination Cascade Reaction

Simlandy, Amit Kumar and Mukherjee, Santanu (2017) Catalytic Enantioselective Synthesis of 3,4-Unsubstituted Thiochromenes through Sulfa-Michael/Julia Kocienski Olefination Cascade Reaction. In: JOURNAL OF ORGANIC CHEMISTRY, 82 (9). pp. 4851-4858.

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Abstract

A highly enantioselective cascade sulfa-Michael/Julia Kocienski olefination reaction between 2-mercap-tobenzaldehydes and beta-substituted vinyl PT-sulfones has been realized for the synthesis of 3,4-unsubstituted 2H-thiochromenes. This reaction, catalyzed by diphenylprolinol TMS ether, proceeds through an aromatic iminium intermediate and furnishes a wide range of 2-substiuted 2H-thiochromenes with excellent enantioselectivities (up to 99:1 er).

Item Type:	Journal Article
Publication:	JOURNAL OF ORGANIC CHEMISTRY
Additional Information:	Copy right for this article belongs to the AMER CHEMICAL SOC, 1155 16TH ST, NW, WASHINGTON, DC 20036 USA
Department/Centre:	Division of Chemical Sciences > Organic Chemistry
Date Deposited:	10 Jun 2017 04:39
Last Modified:	10 Jun 2017 04:39
URI:	http://eprints.iisc.ac.in/id/eprint/57162

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