First asymmetric cascade reaction catalysed by chiral primary aminoalcohols

作者：Arroniz Carlos; Escolano Carmen^*; Luque F Javier; Bosch Joan; Amat Mercedes

来源：Organic and Biomolecular Chemistry, 2011, 9(14): 5079-5085.

DOI：10.1039/c1ob05400g

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.

• 出版日期2011