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

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 delta-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. Copyright (C) 1996 Elsevier Science Ltd