A simple and convenient stereoselective synthesis of [E]-α-methylcinnamic acids via the nucleophilic
addition of hydride ion from sodium borohydride to methyl 3-acetoxy-3-aryl-2-methylenepropanoates
followed by hydrolysis and crystallization is described. Efficacy of this methodology in the synthesis
of [E]-p-(myristyloxy)-α-methylcinnamic acid, an active hypolipidemic agent, and [E]-p-(carbomethoxy)-α-methylcinnamic acid, a valuable synthon for an orally active serine protease inhibitor,
is also demonstrated.
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