Efficient Enantioselective Synthesis of (2S,3R) Methyl β-Hydroxytyrosinate from Achiral Starting Materials

Abstract
Kinetic resolution-epoxidation of the allylic alcohol 4 followed by internal opening of the epoxy N-benzoyl carbamate derived from the epoxide 5 led, after several functional group transformations, to the desired β-hydroxy tyrosine derivative 1b and the useful selectively protected derivatives 12-15.