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trans-5-Substituted 4-pentenoic acids 1a-f and 1h were prepared stereoselectively from 1-substituted propylen-1-ol and triethyl orthoacetate via a Claisen rearrangement followed by basic cleavage of the ethyl ester. For general procedure of Claisen rearrangement involved in this paper, see: Richard, K. H.; Raghovan, S.; Seiji, S. J. Org. Chem. 1972, 37, 3737-3740.
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note
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1H NMR with (R)-(-)-2,2,2-trifluoro-1-(9-anthryl) ethanol. The absolute configuration of the major enantiomer of 2 and 3 was not determined. (d) For determination of absolute configuration, see Supporting Information.
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