An efficient conversion of β-phenylisoserine to β-hydroxyphenylalanine derivatives via aziridines

Department of Chemistry, Indian Institute of Technology, Kanpur-208 016, India

Manuscript received 12 October 1999

β-Phenylisoserine derivatives can be treated with DEAD (diethyl azodicarboxylate)/PPh₃ to afford aziridines which can be regiosp.ecifically opened with oxygen nucleophiles in the presence of catalytic amount of para-toluenesulfonic acid to give the corresponding β-substituled phenylalanine derivatives in good yields. The generality of this transformation is illustrated by converting β-phenylisoserine derived dipeptides to the corresponding β-hydroxyphenylalanine containing dipeptides.