DABCO-Promoted (3 + 2) Annulation of D–A Cyclopropanes with Alkynoates for the Synthesis of Cyclopentenol Derivatives

Abstract

Efficient synthesis of highly functionalized cyclopentenols with an exocyclic Z double bond was investigated via a (3 + 2) annulation reaction of 2-aroyl-D−A (donor−acceptor) cyclopropanes with alkynoates in the presence of DABCO. This synthetic approach featured a wide range of readily available 2-aroyl-substituted D−A cyclopropanes with diverse functional groups, densely substituted cyclopentenols with two stereogenic centers and an exocyclic double bond in a highly stereocontrolled manner and had operationally simple and mild reaction conditions. Note pubs.acs.org/joc