The α-hydroxyphosphonate-phosphate rearrangement of a noncyclic substrate - some new observations.

Racemic ethyl hydrogen (1-hydroxy-2-methylsulfanyl-1-phenylethyl)phosphonate was resolved with (R)-1-phenylethylamine. The (R)-configuration of the (-)-enantiomer was determined by chemical correlation. Esterification of the (-)-enantiomer with a substituted diazomethane derived from 3-hydroxy-1,3,5(10)-estratrien-17-one delivered two epimeric phosphonates separated by HPLC.

Chemical Synthesis of (R)- and (S)-[O,O,O]Phosphoenol Pyruvate.

Enzymes and chirality are intimately associated. For their mechanisms to be studied, chiral substrates are needed as probes. Here, we report a concise synthesis of (R)- and (S)-[O,O,O]phosphoenol pyruvate starting from enantiomerically pure (R)-2-chloro-1-phenylethanol, which was transformed into O-labeled 3-methyl-1-phenylbutane-1,3-diol.