An enantioselective, stereodivergent synthesis of threonine analogs

Article abstract of DOI:10.1016/S0957-4166(96)00518-6

An enantioselective and stereodivergent methedology for the synthesis of the four isomers of P-hydroxy norvaline is presented starting from the common oxazolidin-2-one intermediate 1, via an iterative formation of the oxazolidin-2-one ring to achieve the stereochemical control of the stereogenic centers. The flexibility of the present approach, for the synthesis of several threonine analogs, lies in the ready displacement of the sulfonate group in 2 with the Grignard reagents in the presence of CuI.