Catalytic Enantioselective Elimination of Cyclobutanols
Abstract
Brønsted acid-mediated elimination of alcohols is a fundamental transformation in organic chemistry, yet its application in enantioselective catalysis remains largely unexplored. Here, we report a catalytic, enantioselective elimination of cyclobutanols and their trichloroacetimidate derivatives that afford cyclobutenes bearing all-carbon quaternary stereocenters. Mechanistic studies revealed that a chiral Brønsted acid catalyst mediates concerted, enantioselective elimination of cyclobutanols, whereas their trichloroacetimidates undergo stepwise elimination via a catalyst-substrate covalent intermediate. This research lays the foundation for further investigations of enantioselective elimination reactions.
Fields of Study & Subjects
Asymmetric Hydrogenation and Catalysis
Asymmetric Synthesis and Catalysis
Inorganic and Organometallic Chemistry
Publication details
- Journal / source
- Journal of the American Chemical Society
- Publisher
- American Chemical Society (ACS)
- Volume
- 148
- Issue
- 16
- Pages
- 16568–16575
- Publication date
- 15 April 2026
- Language
- EN