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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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
Publication:	EUROPEAN JOURNAL OF ORGANIC CHEMISTRY
Publisher:	WILEY-V C H VERLAG GMBH
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
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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