1. Diastereoselective Monofluorocyclopropanation Using Fluoromethylsulfonium Salts
- Author
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Arturs Sperga, Renate Melngaile, Kim K. Baldridge, and Janis Veliks
- Subjects
chemistry.chemical_compound ,chemistry ,010405 organic chemistry ,Organic Chemistry ,Rapid access ,Surface modification ,Physical and Theoretical Chemistry ,010402 general chemistry ,01 natural sciences ,Biochemistry ,Combinatorial chemistry ,0104 chemical sciences ,Cyclopropane - 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.
- Published
- 2019