A novel phosphorus-carbon bond formation by ring opening with diethyl phosphite of oxazolines derived from serine

A new reaction of oxazolines derived from serine with diethyl phosphite leading to ring opening products with P–C bond formation is reported. This reaction, which proceeds under neutral conditions and without the use of any halogenated intermediate, results in a mixture of racemic a- and b-phosphono alanines in an approximate 1:2 ratio, with isolated yields up to 77%. The mechanism involves the rearrangement of the oxazoline into the corresponding a-benzamido acrylate, followed by addition of the diethyl phosphite to the double bond. Since no significant transesterification is observed, this method constitutes a simple route for a- and b-phosphono amino acids bearing suitable protecting groups.