Journal of Organic Chemistry p. 353 - 359 (1991)
Update date:2022-08-11
Topics:
Welch, John T.
Plummer, Janet S.
Chou, Tso-Sheng
The ester enolate Claisen rearrangement of allyl α-fluoroacetates 1 forms 2-fluoroalkenoic acids 2 in good to excellent yield with good internal asymmetric induction.This selectivity was unexpected as stereoselective deprotonation of fluoroacetates is not normally possible.The selective formation of the required α-fluoro silyl ketene acetal 3 was found to result from the stereoselective rearrangement of the allyl α-fluoro-α-silylacetate isomer.Although silyl ketene acetals derived from α-fluoropropanoates 7 also rearranged, control of internal asymmetric induction was not possible.
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