Issue 14, 2011

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 aminesvs. 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.

Graphical abstract: First asymmetric cascade reaction catalysed by chiral primary aminoalcohols

Supplementary files

Article information

Article type
Paper
Submitted
14 Mar 2011
Accepted
11 Apr 2011
First published
12 Apr 2011

Org. Biomol. Chem., 2011,9, 5079-5085

First asymmetric cascade reaction catalysed by chiral primary aminoalcohols

C. Arróniz, C. Escolano, F. J. Luque, J. Bosch and M. Amat, Org. Biomol. Chem., 2011, 9, 5079 DOI: 10.1039/C1OB05400G

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