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

Kumar, Akshay; Chimni, Swapandeep Singh

Kumar, Akshay; Chimni, Swapandeep Singh.

Afiliación

Kumar A; Department of Chemistry, U.G.C. Centre of Advance Studies in Chemistry, Guru Nanak Dev University, Amritsar, 143005, India;
Chimni SS; Department of Chemistry, U.G.C. Centre of Advance Studies in Chemistry, Guru Nanak Dev University, Amritsar, 143005, India;

Beilstein J Org Chem ; 10: 929-35, 2014.

Article en En | MEDLINE | ID: mdl-24991242

RESUMEN

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.

Palabras clave

3,3'-disubstituted oxindoles; Michael reaction; organocatalysis; primary-tertiary diamine; spirooxindoles

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Texto completo: 1 Colección: 01-internacional Base de datos: MEDLINE Idioma: En Revista: Beilstein J Org Chem Año: 2014 Tipo del documento: Article Pais de publicación: Alemania

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