2021 journal article

Stereospecific Synthesis of Enantioenriched Alkylidenecyclobutanones via Formal Vinylidene Insertion into Cyclopropanone Equivalents

Organic Letters, 8.

co-author countries: United States of America πŸ‡ΊπŸ‡Έ
Source: ORCID
Added: August 10, 2021

1-Sulfonylcyclopropanols are employed here as efficient cyclopropanone equivalents in a formal vinylidene insertion process, providing the first general synthetic route to enantioenriched alkylidenecyclobutanones. The addition of an alkenyl-Grignard reagent leads to an alkenylcyclopropanol capable of electrophilic activation by N-bromosuccinimide, triggering a regio- and stereospecific 1,2-migration and affording alkylidenecyclobutanones after elimination. Activation of the intermediate with other electrophiles such as HCl or mCPBA leads to the formation of various chiral cyclobutanones and Ξ³-lactones via alternative pathways.