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A new entry to the construction of a quaternary carbon center having a fluorine atom – SN2′ reaction of γ-fluoroallylic alcohol derivatives with various cyanocuprates
Department of Chemistry and Materials Technology, Kyoto Institute of Technology, Matsugasaki, Sakyo-ku, Kyoto 606-0962, Japan
E-mail: konno@chem.kit.ac.jp
Org. Biomol. Chem., 2012,10, 8154-8163
DOI:
10.1039/C2OB25718A
Received
12 Apr 2012,
Accepted
21 Aug 2012
First published online
21 Aug 2012
Treatment of γ-fluoroallylic phosphate with various lower-ordered cyanocuprates derived from Grignard reagents, organolithium, and organozincs gave the corresponding SN2′ products having a fluorine atom at a quaternary carbon center in excellent yields. This system could be successfully extended to the chiral version, enantiomerically pure fluorine-containing materials also being obtained in high yield.
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Organic & Biomolecular Chemistry
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