Ring Enlargements of in Situ-Formed Cyclopropanones by Sulfoxonium Ylides: One-Pot Synthesis of Alkylidene Cyclobutanones
Abstract
A one-pot method for the stereoselective synthesis of alkylidenecyclobutanones from cyclopropanone surrogates is reported. Reaction partners are stable sulfoxonium ylides, leading to the four-membered rings in up to 84% yield. Mechanistic studies indicate that the transformation proceeds via nucleophilic attack of the sulfoxonium ylide on the three-membered ring, followed by ring enlargement. The stereochemical outcome of the ring expansion is substituent-dependent: alkyl groups promote complete retention of configuration, whereas aryl groups result in partial erosion of enantiopurity.
Fields of Study & Subjects
Cyclopropane Reaction Mechanisms
Catalytic Alkyne Reactions
Catalytic C–H Functionalization Methods
Publication details
- Journal / source
- The Journal of Organic Chemistry
- Publisher
- American Chemical Society (ACS)
- Volume
- 91
- Issue
- 8
- Pages
- 3246–3255
- Publication date
- 16 February 2026
- Language
- EN