( S )-2-Benzyl-3-chloropropionic acid (7) was synthesized from ( Z )-2-(chloromethyl)-3-phenylprop-2-enoic acid (5) by asymmetric hydrogenation with a ruthenium 2,2'-bis(di- p -tolylphosphino)-1,1'-binaphthyl complex in the presence of triethylamine. Acetylthiolation then gave 3-acetylthio-2-benzylpropionic acid (2), a subunit of the enkephalinase inhibitor thiorphan (1).
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Yuasa et al. (1998) studied this question.