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Catalytic Asymmetric Michael Addition/Cyclization Cascade Reaction of 3-Isothiocyanatooxindoles with Nitro Olefins

Kayal, Satavisha and Mukherjee, Santanu (2014) Catalytic Asymmetric Michael Addition/Cyclization Cascade Reaction of 3-Isothiocyanatooxindoles with Nitro Olefins. In: EUROPEAN JOURNAL OF ORGANIC CHEMISTRY (30). pp. 6696-6700.

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Official URL: http://dx.doi.org/ 10.1002/ejoc.201402534

Abstract

The first organocatalytic asymmetric reaction of 3-isothiocyanatooxindoles with nitro olefins has been developed by using a cinchonidine-derived bifunctional catalyst. The resulting products, highly functionalized 3,2-pyrrolidinyl-substituted spirooxindole derivatives, were obtained in high yields with good diastereo- and enantioselectivities (up to dr >20:1 and er = 96:4). This Michael addition/cyclization cascade reaction employs monosubstituted nitro olefins and complements the Zn-II-catalyzed variant, which is only applicable to disubstituted nitro olefins.

Item Type: Journal Article
Additional Information: Copy right for this article belongs to the WILEY-V C H VERLAG GMBH, BOSCHSTRASSE 12, D-69469 WEINHEIM, GERMANY
Keywords: Asymmetric catalysis; Cascade reactions; Nitrogen heterocycles; Michael addition; Spiro compounds
Department/Centre: Division of Chemical Sciences > Organic Chemistry
Depositing User: Id for Latest eprints
Date Deposited: 04 Dec 2014 04:49
Last Modified: 04 Dec 2014 04:49
URI: http://eprints.iisc.ac.in/id/eprint/50368

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