Journal
JOURNAL OF THE AMERICAN CHEMICAL SOCIETY
Volume 135, Issue 21, Pages 7819-7822Publisher
AMER CHEMICAL SOC
DOI: 10.1021/ja402393w
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Funding
- Natural Science and Engineering Research Council of Canada (NSERC)
- Canada Foundation for Innovation
- Canada Research Chair Program
- Centre in Green Chemistry and Catalysis (CGCC)
- Universite de Montreal
- NSERC (PGS D)
- Genentech
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Highly enantio- and diastereoenriched monofluorocyclopropanes were accessed via the Simmons-Smith fluorocyclopropanation of allylic alcohols using difluoroiodomethane and ethylzinc iodide as the substituted carbenoid precursors. The scrambling of halogens at the zinc carbenoid led to the formation of the fluorocyclopropanating agent (fluoroiodomethyl)zinc-(II) fluoride. This strategy circumvented the ongoing limitation in Simmons-Smith fluorocyclopropanations relying on the use of the relatively inaccessible and expensive carbenoid precursor fluorodiiodomethane.
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