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Updated: Jun 1, 2026

Enzymatic Cascade Reactions for the Synthesis of Chiral Amino Alcohols from L-lysine
Published on: February 16, 2018
First asymmetric cascade reaction catalysed by chiral primary aminoalcohols
Carlos Arróniz1, Carmen Escolano, F Javier Luque
1Laboratory of Organic Chemistry, Faculty of Pharmacy, and Institute of Biomedicine (IBUB), 08028 Barcelona, Spain.
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.
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