Asymmetric synthesis of CF <sub>2</sub> -functionalized aziridines by combined strong Brønsted acid catalysis
Xing-Fa Tan, Fa‐Guang Zhang, Jun‐An Ma
Abstract
A diastereo- and enantioselective approach to access chiral CF 2 -functionalized aziridines from difluorodiazoethyl phenyl sulfone (PhSO 2 CF 2 CHN 2 ) and in situ-formed aldimines is described. This multicomponent reaction is enabled by a combined strong Brønsted acid catalytic platform consisting of a chiral disulfonimide and 2-carboxyphenylboronic acid. The optical purity of the obtained CF 2 -substituted aziridines could be further improved by a practical dissolution–filtration procedure.
Topics & Concepts
ChemistryEnantioselective synthesisBrønsted–Lowry acid–base theoryCatalysisAldimineSulfoneOrganocatalysisCombinatorial chemistryReaction conditionsOrganic chemistrySynthesis and Catalytic ReactionsFluorine in Organic ChemistrySulfur-Based Synthesis Techniques