Work

Catalytic Enantioselective Elimination of Cyclobutanols

Year: 2026

Type: article

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.

Source: Journal of the American Chemical Society

DOI: 10.1021/jacs.5c22741

Authors: Pravin Kumar, Howard Díaz-Salazar, Anna Iagarmina, Łukasz Woźniak

Institution: Jagiellonian University

Language: English

Topic: Asymmetric Synthesis and Catalysis

Subfield: Organic Chemistry

Field: Chemistry

Domain: Physical Sciences

Open Access status: hybrid

Estimated APC paid: $4,500

Funders: Narodowe Centrum Nauki, Uniwersytet Jagielloński w Krakowie