Efficient direct asymmetric vinylogous Michael addition reactions of γ-butenolides to chalcones catalyzed by vicinal primary-diamine salts
- 19 February 2010
- journal article
- Published by Royal Society of Chemistry (RSC) in Chemical Communications
- Vol. 46 (12), 2124-2126
- https://doi.org/10.1039/b923925a
Abstract
The first direct organocatalytic asymmetric vinylogous Michael addition reactions of γ-butenolides to chalcones have been developed by using chiral 1,2-diaminocyclohexane as a novel organocatalyst via a di-iminium transition state to provide syn-Michael products with good yields, high diastereoselectivities and enantioselectivities (up to 78% yield, >99:1 dr and 96% ee).Keywords
This publication has 50 references indexed in Scilit:
- Pulvinones as bacterial cell wall biosynthesis inhibitorsBioorganic & Medicinal Chemistry Letters, 2005
- Structure and anti-HIV activity of micrandilactones B and C, new nortriterpenoids possessing a unique skeleton from Schisandra micranthaChemical Communications, 2005
- Vitamin C and 6-amino-vitamin C conjugates of diclofenac: synthesis and evaluationInternational Journal of Pharmaceutics, 2005
- Steroids: reactions and partial synthesisNatural Product Reports, 2002
- Novel Polyketide Metabolites from a Species of Marine FungiJournal of Natural Products, 1999
- Comparison of Ectoparasites Infestation for Fresh and Saltwater Fishes from Euphrates, and Razzaza Lake, IraqJournal of Natural Products, 1999
- The natural products chemistry of West Indian gorgonian octocoralsTetrahedron, 1995
- Lipase-catalyzed kinetic resolution of methyl 4-hydroxy-5-tetradecynoate and its application to a facile synthesis of japanese beetle pheromoneTetrahedron, 1991
- Synthesis of optically active pheromonesTetrahedron, 1989
- Recent advances in the chemistry of unsaturated lactonesChemical Reviews, 1976