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Catalytic Asymmetric Direct Vinylogous Michael Addition of gamma-Aryl-Substituted Deconjugated Butenolides to Nitroolefins and N-Phenylmaleimide

Kumar, Vikas and Ray, Bidisha and Rathi, Preeti and Mukherjee, Santanu (2013) Catalytic Asymmetric Direct Vinylogous Michael Addition of gamma-Aryl-Substituted Deconjugated Butenolides to Nitroolefins and N-Phenylmaleimide. In: SYNTHESIS-STUTTGART, 45 (12). pp. 1641-1646.

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Official URL: http://dx.doi.org/10.1055/s-0033-1338705

Abstract

Direct asymmetric vinylogous Michael reactions of gamma-aryl-substituted deconjugated butenolides with nitroolefins and N-phenylmaleimide are described using bifunctional thiourea derivatives as the catalyst. The resulting butenolide derivatives containing adjacent quaternary and tertiary stereocenters are obtained in good yields (54-90%) and with excellent enantioselectivities (er up to 99:1) and high diastereoselectivities (dr up to > 20:1).

Item Type: Journal Article
Additional Information: Copyright for this article belongs to GEORG THIEME VERLAG KG, GERMANY.
Keywords: Michael reaction; butenolide; quaternary stereocenter; nitroolefin; maleimide
Department/Centre: Division of Chemical Sciences > Organic Chemistry
Depositing User: Id for Latest eprints
Date Deposited: 09 Sep 2013 10:09
Last Modified: 09 Sep 2013 10:09
URI: http://eprints.iisc.ac.in/id/eprint/47074

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