Facile and Convenient One-Pot Process for the Synthesis of Spirooxindole Derivatives in High Optical Purity Using (？)-(S)-Brevicolline as an Organocatalyst.docVIP

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Facile and Convenient One-Pot Process for the Synthesis of Spirooxindole Derivatives in High Optical Purity Using (？)-(S)-Brevicolline as an Organocatalyst.doc

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Facile and Convenient One-Pot Process for the Synthesis of Spirooxindole Derivatives in High Optical Purity Using (？)-(S)-Brevicolline as an Organocatalyst

Symmetry 2011, 3, 165-170; doi:10.3390/sym3020165 OPEN ACCESS symmetry ISSN 2073-8994 /journal/symmetry Article Facile and Convenient One-Pot Process for the Synthesis of Spirooxindole Derivatives in High Optical Purity Using (?)-(S)-Brevicolline as an Organocatalyst Fliur Macaev *, Natalia Sucman, Felix Shepeli, Marina Zveaghintseva and Vsevolod Pogrebnoi Academy Street 3, Institute of Chemistry, Academy of Science of Moldova, MD-2028 Chisinau, Moldova; E-Mails: nicheli@yandex.ru (N.S.); dianashepel@mail.ru (F.S.); mari6azv@mail.ru (M.Z.); seva.antivirus@ (V.P.) * Author to whom correspondence should be addressed; E-Mail: flmacaev@cc.acad.md; Tel.: +373-22-73-97-54; Fax: +737-22-73-99-54. Received: 10 March 2011; in revised form: 11 April 2011 / Accepted: 12 April 2011 / Published: 20 April 2011 Abstract: The paper presents an application of the asymmetry approach to spirooxindoles via Brevicolline, Cinchonidine or Cinchonine catalyzed one-pot multicomponent synthesis. Brevicolline, in comparison with Cinchonidine or Cinchonine, catalyzes the reaction of isatins, acetylacetone/ethyl 3-oxobutanoate and malononitrile, with the formation of spiro[oxindole-3,4-4H-pirane] derivatives in an optically active form in very good to excellent yields. Keywords: organocatalyzed reactions; spiro[oxindole-3,4-4H-pyrane]; Brevicolline; Cinchonidine; Cinchonine 1. Introduction Asymmetric catalysis with the participation of organic compounds is one of the most rapidly developing areas of modern chemistry [1–5]. A special position among these catalysts is occupied by alkaloids, with the vast majority of research, until recently, being focused on the discovery of new properties of the well-studied cinchona alkaloids and related compounds [6–11]. The cupreine-catalyzed synthesis of optically active spiro[pyran-oxindoles] as promising candidates for chemical biology and drug discovery has b