Enantioselective introduction of fluoride into organic compounds: First asymmetric ring opening of epoxides by hydrofluorinating reagents
S Bruns, G Haufe
Index: Bruns, Stefan; Haufe, Guenter Journal of Fluorine Chemistry, 2000 , vol. 104, # 2 p. 247 - 254
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Citation Number: 75
Abstract
The first enantioselective epoxide ring opening with hydrofluorinating agents mediated by chiral non-racemic Lewis acids is reported. The reaction of cyclohexene oxide (1) with KHF2/18-crown-6 is trans-diastereoselective and proceeds with 55% ee to form (R, R)-(−)-2- fluorocyclohexanol (2) in the presence of Jacobsen's (S, S)-(+)-(salen) chromium chloride complex A. From racemic epoxides such as styrene oxide (9) or phenyl glycidether (13), ...
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