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Enantioselective Synthesis of Functionalized beta-Lactones by NHC-Catalyzed Aldol Lactonization of Ketoacids

Mondal, Santigopal and Mukherjee, Subrata and Das, Tamal Kanti and Gonnade, Rajesh G and Biju, Akkattu T (2017) Enantioselective Synthesis of Functionalized beta-Lactones by NHC-Catalyzed Aldol Lactonization of Ketoacids. In: JOURNAL OF ORGANIC CHEMISTRY, 82 (17). pp. 9223-9228.

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Official URL: http://doi.org/10.1021/acs.joc.7b01526

Abstract

N-Heterocyclic carbene (NHC)-catalyzed intramolecular aldol lactonization of readily available ketoacids leading to the enantioselective synthesis of cyclopentane-fused beta-lactones is presented. The reaction proceeds via the generation of NHC-bound enolate intermediates formed from the ketoacids in the presence of the peptide coupling reagent HATU and NHC generated from the chiral triazolium salt. The functionalized beta-lactones are formed under mild conditions in high yields and enantioselectivities.

Item Type: Journal Article
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
Depositing User: Id for Latest eprints
Date Deposited: 07 Oct 2017 06:06
Last Modified: 07 Oct 2017 06:06
URI: http://eprints.iisc.ac.in/id/eprint/57987

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