title: Primary-tertiary diamine-catalyzed Michael addition of ketones to isatylidenemalononitrile derivatives.
abstract: 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.
authors.affiliation: Department of Chemistry, U.G.C. Centre of Advance Studies in Chemistry, Guru Nanak Dev University, Amritsar, 143005, India;
authors.forename: Akshay
authors.initials: A
authors.lastname: Kumar
authors.affiliation: Department of Chemistry, U.G.C. Centre of Advance Studies in Chemistry, Guru Nanak Dev University, Amritsar, 143005, India;
authors.forename: Swapandeep Singh
authors.initials: SS
authors.lastname: Chimni
keywords: 3,3'-disubstituted oxindoles; Michael reaction; organocatalysis; primary-tertiary diamine; spirooxindoles