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

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).