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Enantioselective Lewis Base Catalyzed Phosphonyldifluoromethylation of Allylic Fluorides.pdf (810.55 kB)
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Enantioselective Lewis Base Catalyzed Phosphonyldifluoromethylation of Allylic Fluorides Using C-Silyl Latent Pronucleophile

preprint
submitted on 17.03.2020 and posted on 19.03.2020 by You Zi, Markus Lange, Ivan Vilotijevic
The first enantioselective phosphonyldifluoromethylation is enabled by the use of diethyl (difluoro(trimethylsilyl)methyl)pho-sphonate reagent as a latent pronuclephile in Lewis base catalyzed substitution of allylic fluorides. The reactions proceed as 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.

Funding

Carl Zeiss Foundation

Friedrich Schiller University Jena

State of Thuringia

History

Email Address of Submitting Author

ivan.vilotijevic@uni-jena.de

Institution

Friedrich Schiller University Jena

Country

Germany

ORCID For Submitting Author

0000-0001-6199-0632

Declaration of Conflict of Interest

No conflict of interest.

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