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Dual Iminium- and Lewis Base Catalyzed Morita-Baylis-Hillman Reaction on Cyclopent-2-enone

Riccardo Innocenti, Gloria Menchi, Andrea Trabocchi*

*Department of Chemistry "Ugo Schiff", University of Florence, Via della Lastruccia 13, 50019 Sesto Fiorentino, Florence, Italy, Email: andrea.trabocchiunifi.it

R. Innocenti, G. Menchi, A. Trabocchi, Synlett, 2018, 29, 820-824.

DOI: 10.1055/s-0036-1591521 (free Supporting Information)


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Abstract

Iminium catalysis of the challenging Morita-Baylis-Hillman reaction of cyclopenten-2-one provides allylic alcohols in excellent yields. Experimental evidence shows that secondary amines act as co-catalysts activating the enone moiety towards the nucleophilic attack at the β-position by DABCO as the Lewis base catalyst.

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proposed mechanism



Key Words

organocatalysis, cyclopentenones, synthetic methods, C-C coupling, basicity, Baylis-Hillman Reaction


ID: J60-Y2018