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Primary-tertiary diamine-catalyzed Michael addition of ketones to isatylidenemalononitrile derivatives

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      Simple primary-tertiary diamines easily derived from natural primary amino acids were used to catalyze the Michael addition of ketones with isatylidenemalononitrile derivatives. Diamine 1a in combination with D-CSA as an additive provided Michael adducts in high yield (up to 94%) and excellent enantioselectivity (up to 99%). The catalyst 1a was successfully used to catalyze the three-component version of the reaction by a domino Knoevenagel–Michael sequence. The Michael adduct 4a was transformed into spirooxindole 6 by a reduction with sodium borohydride in a highly enantioselective manner.

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      The 3,3'-pyrrolidinyl-spirooxindole unit is a privileged heterocyclic motif that forms the core of a large family of alkaloid natural products with strong bioactivity profiles and interesting structural properties. Significant recent advances in the synthesis of this fused heterocyclic system have led to intense interest in the development of related compounds as potential medicinal agents or biological probes.
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            Author and article information

            Affiliations
            [1 ]Department of Chemistry, U.G.C. Centre of Advance Studies in Chemistry, Guru Nanak Dev University, Amritsar, 143005, India; Fax: (+)91-183-2258820
            Contributors
            Role: Associate Editor
            Journal
            Beilstein J Org Chem
            Beilstein J Org Chem
            Beilstein Journal of Organic Chemistry
            Beilstein-Institut (Trakehner Str. 7-9, 60487 Frankfurt am Main, Germany )
            1860-5397
            2014
            24 April 2014
            : 10
            : 929-935
            24991242 4077384 10.3762/bjoc.10.91
            Copyright © 2014, Kumar and Chimni; licensee Beilstein-Institut.

            This is an Open Access article under the terms of the Creative Commons Attribution License ( http://creativecommons.org/licenses/by/2.0), which permits unrestricted use, distribution, and reproduction in any medium, provided the original work is properly cited.

            The license is subject to the Beilstein Journal of Organic Chemistry terms and conditions: ( http://www.beilstein-journals.org/bjoc)

            Categories
            Full Research Paper
            Chemistry
            Organic Chemistry

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