Abstract
( Z)- β-Fluoromethylene- m-tyrosine (2) has been prepared by acid hydrolysis of ethyl 2-trifluoroacetylamino-3-(3-methoxyphenyl)-4-fluoro-3-butenoate ( 1) and its structure established by single crystal X-ray diffraction analysis. Fluorination of the amino acid 2 with acetyl hypofluorite yielded a mixture of products containing fluorine substituted on the ring ( 3a-c) as well as added across the vinylic double bond ( 4a,b). The mechanism for the formation of the diastereomeric adducts 4a and 4b is discussed based on tight ion pair intermediates. All major products of fluorination of 2 were isolated by semipreparative HPLC and their structures determined by spectral analyses.
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