Enantioselective Direct Vinylogous Michael Addition of Functionalized Furanones to Nitroalkenes Catalyzed by an Axially Chiral Guanidine Base

Abstract

The highly syn-diastereo- and enantioselective direct vinylogous Michael addition of α-thio substituted furanones with conjugate nitroalkenes was demonstrated using an axially chiral guanidine base catalyst. The method provides facile access to enantioenriched α,γ-functionalized butenolides that can be further manipulated, thereby rendering them useful synthetic intermediates.