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N-Heterocyclic Carbene-Catalyzed Michael-Michael-Lactonization Cascade for the Enantioselective Synthesis of Tricyclic delta-Lactones

Mukherjee, Subrata and Ghosh, Arghya and Marelli, Udaya Kiran and Biju, Akkattu T (2018) N-Heterocyclic Carbene-Catalyzed Michael-Michael-Lactonization Cascade for the Enantioselective Synthesis of Tricyclic delta-Lactones. In: ORGANIC LETTERS, 20 (10). pp. 2952-2955.

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Official URL: https://dx.doi.org/10.1021/acs.orglett.8b00998

Abstract

Enantioselective synthesis of tricyclic delta-lactones with three contiguous stereocenters has been demonstrated by the N-heterocyclic carbene (NHC)-catalyzed functionalization of benzylic C(sp(3))-H bonds. The NHC-catalyzed reaction of enals with dinitrotoluene derivatives under oxidative conditions proceeds via the chiral alpha,beta-unsaturated acylazoliums and produces the delta-lactones in good yields and excellent diastereoselectivity and enantioselectivity. This mild and atom-economic cascade reaction takes place in a Michael/Michael/lactonization sequence and tolerates a broad range of functional groups.

Item Type: Journal Article
Additional Information: Copyright of this article belong to AMER CHEMICAL SOC, 1155 16TH ST, NW, WASHINGTON, DC 20036 USA
Department/Centre: Division of Chemical Sciences > Organic Chemistry
Depositing User: Id for Latest eprints
Date Deposited: 17 Jul 2018 15:27
Last Modified: 17 Jul 2018 15:27
URI: http://eprints.iisc.ac.in/id/eprint/60200

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