Enantioselective α,α-Chlorofluorination of Sulfoxonium Ylides

Key Points

The enantioselective α,α-chlorofluorination yielded gem-dihalogenated compounds in up to 90% yield.
Chiral aminosulfoxonium ylides provided up to 96:4 enantioselectivity with the fluorinating reagent.
Reaction methods include the use of chiral fluorinating reagents prepared in situ from cinchona alkaloids.
These results suggest that utilizing chiral ylides can significantly enhance selectivity in halogenation reactions.

Abstract

The first examples of enantioselective α,α-chlorofluorination of α-carbonylsulfoxonium ylides are described. Herein, two modes of reaction are explored, using chiral aminosulfoxonium ylides and a chiral fluorinating reagent, prepared in situ from commercially available cinchona alkaloids. Using these approaches, 25 examples of gem-dihalogenated compounds (including bromochlorination) were obtained in good yields (up to 90%) and enantioselectivity (up to 96:4 er).

Enantioselective α,α-Chlorofluorination of Sulfoxonium Ylides

Key Points

Abstract

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