The unique chemistry of alkylidene beta-ketoesters has been explored under catalytic Lewis acidic conditions to generate a variety of cyclic and bicyclic compounds. These compounds can be obtained through simple Knoevenagel condensation of an aromatic beta-ketoester and an aldehyde. Depending on the substitution of the aldehyde, various products can be obtained including highly diatereoselective cyclohexyl halides, spirofused indanones, as well as [4,3,1] bicyclic ring systems.  This strategy can be used to produce one carbon-carbon bond and one carbon halide bond or can be used for the production of two new carbon-carbon bonds.

Cationic cyclizations of alkylidene beta-ketoesters

256th National Meeting (2018)

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