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Diastereoselective Monofluorocyclopropanation Using Fluoromethylsulfonium Salts
Renate Melngaile1, Arturs Sperga1, Kim K Baldridge2
1Latvian Institute of Organic Synthesis, Aizkraukles 21, LV-1006 Riga, Latvia.
Abstract:
Diarylfluoromethylsulfonium salts, alternatives to freons or advanced fluorinated building blocks, are bench stable and easy-to-use sources of direct fluoromethylene (:CHF) transfer to alkenes. These salts enabled development of a trans-selective monofluorinated Johnson-Corey-Chaykovsky reaction with vinyl sulfones or vinyl sulfonamides to access synthetically challenging monofluorocyclopropane scaffolds. The described method offers rapid access to monofluorinated cyclopropane building blocks with further functionalization opportunities to deliver more complex synthetic targets diastereoselectively.
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