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Updated: Oct 25, 2025
A Two-Step Protocol for Umpolung Functionalization of Ketones Via Enolonium Species
Published on: August 16, 2018
Catalytic, Enantioselective Syn-Oxyamination of Alkenes
Emily M Mumford1, Brett N Hemric1, Scott E Denmark1
1Roger Adams Laboratory, Department of Chemistry, University of Illinois, Urbana, Illinois 61801, United States.
Abstract:
The chemo-, regio-, diastereo-, and enantioselective 1,2-oxyamination of alkenes using selenium(II/IV) catalysis with a chiral diselenide catalyst is reported. This method uses N-tosylamides to generate oxazoline products that are useful both as protected 1,2-amino alcohol motifs and as chiral ligands. The reaction proceeds in good yields with excellent enantio- and diastereoselectivity for a variety of alkenes and pendant functional groups such as sulfonamides, alkyl halides, and glycol-protected ketones. Furthermore, the rapid generation of oxazoline products is demonstrated in the expeditious assembly of chiral PHOX ligands as well as diversely protected amino alcohols.
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