A highly enantioselective synthesis of phosphate triesters

Article abstract of DOI:10.1021/ja00175a030

A general methodology for the preparation of both enantiomers of a variety of trialkyl phosphates with enantiomeric excesses ranging from 87 to 92% is described. Bis(2,4-dichlorophenyl) phosphoramidates bearing a 2-substituted pyrrolidine moiety as the chiral auxiliary are prepared and examined for their stereoselectivity. Considerations based on both the absolute configuration of the product phosphates as well as the X-ray structural determination of one of the bis(2,4-dichlorophenyl) phosphoramidates suggest these substitutions occur with preponderant inversion of configuration at phosphorus.