Enantioselective Synthesis of Tricyclic β-Lactones by NHC-Catalyzed Desymmetrization of Cyclic 1,3-Diketones

Shee, S and Mukherjee, S and Gonnade, RG and Biju, AT (2020) Enantioselective Synthesis of Tricyclic β-Lactones by NHC-Catalyzed Desymmetrization of Cyclic 1,3-Diketones. In: Organic Letters, 22 (14). pp. 5407-5411.

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Abstract

The NHC-catalyzed desymmetrization of cyclic-1,3-diketones allowing the enantioselective construction of tricyclic β-lactones with five contiguous stereocenters, including two quaternary stereocenters, has been developed. The mild and operationally simple addition of α-bromoenals to cyclopentane-1,3-diketone derivatives proceeds via the initial formation of chiral α,β-unsaturated acylazolium intermediates and culminates in a cascade reaction, following the Michael-aldol-lactonization pathway to deliver the β-lactone derivatives in moderate to good yields and excellent selectivity. © 2020 American Chemical Society.

Item Type:	Journal Article
Publication:	Organic Letters
Publisher:	American Chemical Society
Additional Information:	copy right for this article belongs to American Chemical Society
Department/Centre:	Division of Chemical Sciences > Organic Chemistry
Date Deposited:	11 Nov 2020 06:28
Last Modified:	11 Nov 2020 06:28
URI:	http://eprints.iisc.ac.in/id/eprint/66119

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