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Organocatalytic Enantioselective Vinylogous Michael-AIdoI Cascade for the Synthesis of Spirocyclic Compounds

Mondal, Santigopal and Mukherjee, Subrata and Yetra, Santhivardhana Reddy and Gonnade, Rajesh G and Biju, Akkattu T (2017) Organocatalytic Enantioselective Vinylogous Michael-AIdoI Cascade for the Synthesis of Spirocyclic Compounds. In: ORGANIC LETTERS, 19 (16). pp. 4367-4370.

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Official URL: http://doi.org/10.1021/acs.orglett.7b02085

Abstract

Enantioselective synthesis of pyrazolone-fused spirocyclohexenols by the secondary amine-catalyzed cascade reaction of alpha,beta-unsaturated aldehydes with alpha-arylidene pyrazolinones is reported. This formal 3 + 3] organocascade reaction proceeds through a vinylogous Michael-aldol sequence to furnish the spiroheterocycles with three stereocenters including an all-carbon quaternary center in good yields and selectivities. The catalytic generation of alpha,beta-unsaturated iminium ions from enals and tandem dienolate/enolate formation from pyrazolinones are the key for the success of this spiroannulation reaction.

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: 16 Sep 2017 06:17
Last Modified: 16 Sep 2017 06:17
URI: http://eprints.iisc.ac.in/id/eprint/57816

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