Asymmetric vinylogous Michael reaction of α,β-unsaturated ketones with γ-butenolide under multifunctional catalysis?

Chemical Communications Pub Date: 2010-07-02 DOI: 10.1039/C0CC01054E

Abstract

A general and direct organocatalytic asymmetric vinylogous Michael reaction of γ-butenolide with α,β-unsaturated ketones was investigated with a multifunctional primary amine salt as catalyst. The reaction enables straightforward access toward synthetically versatile γ-substituted butenolides from simple 2(5H)-furanone with satisfactory yields, diastereo- and enantioselectivities (up to 30?:?1 dr and 95–99% ee).

Graphical abstract: Asymmetric vinylogous Michael reaction of α,β-unsaturated ketones with γ-butenolide under multifunctional catalysis
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