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Updated: May 15, 2026

A Two-Step Protocol for Umpolung Functionalization of Ketones Via Enolonium Species
Published on: August 16, 2018
Catalytic enantioselective cyclization and C3-fluorination of polyenes
Nikki A Cochrane1, Ha Nguyen, Michel R Gagne
1Department of Chemistry, University of North Carolina at Chapel Hill, CB # 3290, Chapel Hill, North Carolina 27599, USA.
Abstract:
(Xylyl-phanephos)Pt(2+) in combination with XeF(2) mediates the consecutive diastereoselective cation-olefin cyclization/fluorination of polyene substrates. Isolated yields were typically in the 60-69% range while enantioselectivities reached as high as 87%. The data are consistent with a stereoretentive fluorination of a P(2)Pt-alkyl cation intermediate.
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