Enantioselective synthesis of phosphinyl peptidomimetics via an asymmetric Michael reaction of phosphinic acids with acrylate derivatives

Asymmetric Michael reaction of phosphinic or aminophosphinic acids with acrylate derivatives afforded phosphinyl dipeptidomimetics in excellent yields (>90%). Chiral induction of substituents at the α-position of acrylate derivatives of Evans oxazolidinone type auxiliaries was obtained in moderate to excellent diastereomeric and enantiomeric excesses (50–98%). Pure diastereomers and enantiomers of phosphinyl dipeptidomimetics 16–19 were also successfully separated by HPLC.