Journal
JOURNAL OF FLUORINE CHEMISTRY
Volume 104, Issue 2, Pages 247-254Publisher
ELSEVIER SCIENCE SA
DOI: 10.1016/S0022-1139(00)00249-9
Keywords
fluorohydrins; epoxide ring opening; enantioselectivity; (salen)chromium complex; hydrofluorination
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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), mainly or exclusively the products with fluorine in primary position are formed with 90 or 62% ee, respectively. In all cases minor amounts of corresponding chlorohydrins are formed. (C) 2000 Elsevier Science S.A. All rights reserved.
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