Hydroboration of vinylglycine and allylglycine as a route to boron- derivatives of α-amino acids

Article abstract of DOI:10.1016/0040-4039(96)01062-3

The hydroboration of protected vinylglycine and allylglycine with dicyclohexyl- or diisopinocampheylborane occurs chimio- and regioselectively with attachment of boron to the less substituted end of the carbon-carbon double bond. Homoserine or δ-hydroxynorvaline are readily obtained by H₂O₂/CH₃CO₂Na oxidation of dicyclohexylborane derivatives and 2-amino-4- boronobutanoic acid or 2-amino-5-boronopentanoic acid by reaction of diisopinocampheylborane derivatives with excess of ethanal and deprotection.