Combined application of organozinc chemistry and one-pot hydroboration–Suzuki coupling to the synthesis of amino acids

Abstract

Hydroboration using 9-BBN-H of the protected enantiomerically pure but-3-enylglycine derivative 11, prepared by copper-catalysed allylation of the serine-derived organozinc reagent 1, followed by Suzuki coupling of the derived borane with a variety of aromatic halides, 2-bromopyridine and 2-bromopropene gives the protected amino acids 14a–l and 15. This method augments our previous methods for the synthesis of phenylalanine homologues.