Lewis acid-catalyzed diastereoselective formal ene reaction of thioindolinones/thiolactams with bicyclobutanes

Guin, A and Deswal, S and Harariya, MS and Biju, AT (2024) Lewis acid-catalyzed diastereoselective formal ene reaction of thioindolinones/thiolactams with bicyclobutanes. In: Chemical Science, 15 (31). pp. 12473-12479.

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Abstract

Bicyclo1.1.0butanes (BCBs), featuring two fused cyclopropane rings, have found widespread application in organic synthesis. Their versatile reactivity towards radicals, nucleophiles, cations, and carbenes makes them suitable for various reactions, including ring-opening and annulation strategies. Despite this versatility, their potential as enophiles in an ene reaction remains underexplored. Considering this and given the challenges of achieving diastereoselectivity in ring-opening reactions of BCBs, herein, we present a unique method utilizing BCBs as enophiles in a mild and diastereoselective Sc(OTf)3-catalyzed formal ene reaction with thioindolinones/thiolactams, delivering 1,3-disubstituted cyclobutane derivatives in high yields and excellent regio- and diastereoselectivity. Notably, structurally different thiolactam derivatives underwent diastereoselective addition to BCBs, affording the corresponding cyclobutanes. The synthesized thioindole-substituted cyclobutanes could serve as a versatile tool for subsequent functional group manipulations. © 2024 The Royal Society of Chemistry.

Item Type:	Journal Article
Publication:	Chemical Science
Publisher:	Royal Society of Chemistry
Additional Information:	The copyright for this article belongs to Royal Society of Chemistry.
Keywords:	Stereoselectivity, Carbenes; Cyclobutanes; Cyclopropane ring; Diastereoselective; Diastereoselectivities; Ene reaction; Lewis Acid; Organic synthesis; Ring opening; Ring opening reaction, Positive ions
Department/Centre:	Division of Chemical Sciences > Organic Chemistry
Date Deposited:	18 Dec 2024 10:15
Last Modified:	18 Dec 2024 10:15
URI:	http://eprints.iisc.ac.in/id/eprint/85880

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