The β,γ-unsaturated butenolides have attracted great attention recently due to their direct ability for construction of γ,γ-disubstituted butenolide derivatives, which are important motifs in the biologically active natural compounds and pharmaceutically useful molecules. A highly efficient N,N′-dioxide–Scandium(III) complex catalytic system has been developed for the asymmetric vinylogous Michael reaction of the α-angelica lactone and its derivatives to α,β-unsaturated-γ-keto esters, affording the corresponding γ,γ-disubstituted butenolide products in moderate to good yields (up to 93%) with high dr (up to &gt;19:1) and ee values (up to 97%) under mild reaction conditions.

N,N′-dioxide–scandium(III) catalyzed asymmetric Michael addition of β,γ-unsaturated butenolides to α,β-unsaturated-γ-keto esters

251st National Meeting (2016)

The official archive and repository for all ACS Meetings & Expositions abstracts and select posters or presentations.