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

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          Summary

          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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          Pyrrolidinyl-spirooxindole natural products as inspirations for the development of potential therapeutic agents.

          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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            Construction of Spiro[pyrrolidine-3,3′-oxindoles] − Recent Applications to the Synthesis of Oxindole Alkaloids

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              Asymmetric Syntheses of Oxindole and Indole Spirocyclic Alkaloid Natural Products

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                Author and article information

                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
                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
                Article
                10.3762/bjoc.10.91
                4077384
                24991242
                29038d19-9b64-4773-9700-64e25a2c4075
                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)

                History
                : 1 February 2014
                : 2 April 2014
                Categories
                Full Research Paper
                Chemistry
                Organic Chemistry

                Organic & Biomolecular chemistry
                3,3'-disubstituted oxindoles,michael reaction,organocatalysis,primary-tertiary diamine,spirooxindoles

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