title: First asymmetric cascade reaction catalysed by chiral primary aminoalcohols.
abstract: Readily available chiral primary 1,2-aminoalcohols and diamines have been explored as organocatalysts for a domino Michael-aldol reaction. Their application in this organocascade process afforded cyclohexanone A with high levels of reactivity (up to 91% yield) and stereoselectivity (>97 : 3 d.r., up to 93% ee). Depending on the acid cocatalyst different chiral species (cyclic secondary amines vs. acyclic primary amines) might catalyse the process. In order to shed light on the catalytic activation, several experiments were carried out and a detailed possible reaction mechanism is proposed. Theoretical studies support the stereochemical outcome of the process.
authors: Laboratory of Organic Chemistry, Faculty of Pharmacy, and Institute of Biomedicine (IBUB), 08028 Barcelona, Spain.
authors: Carlos
authors: C
authors: Arróniz
authors: Carmen
authors: C
authors: Escolano
authors: F Javier
authors: FJ
authors: Luque
authors: Joan
authors: J
authors: Bosch
authors: Mercedes
authors: M
authors: Amat