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 |
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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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