Journal
CHEMICAL COMMUNICATIONS
Volume 56, Issue 42, Pages 5689-5692Publisher
ROYAL SOC CHEMISTRY
DOI: 10.1039/d0cc01815e
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Funding
- Carl-Zeiss Foundation
- Friedrich Schiller University Jena
- State of Thuringia
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The first enantioselective phosphonyldifluoromethylation is enabled by the use of diethyl (difluoro(trimethylsilyl)-methyl)phosphonate reagent as a latent pronucleophile in the Lewis base catalyzed substitution of allylic fluorides. The reaction proceeds as a kinetic resolution to produce both the difluoromethylphosphonate products and the remaining fluorides in good yields and with high stereoselectivity. The use of cinchona based alkaloid catalysts enables the facile synthesis of both enantiomers of the difluoromethylphosphonate products.
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