Stereocontrolled Synthesis of R or S Diphenylphosphinoyl Hydroxy Aldehydes and 1,2-Diols Using Bicyclic Aminals

Article abstract of DOI:10.1016/0040-4039(95)00334-9

Homochiral diphenylphosphinoyl hydroxy aldehydes 1 and 2 have been made by diastereoselective additions of metallated methyldiphenylphosphine oxides 10 to Mukaiyama's keto aminals 8 and 9.Reduction to diphenylphosphinoyl 1,2 diols 3 and 4 is also described.Sharpless asymmetric dihydroxylation provides an alternative route diphenylphosphinoyl 1,2 diols 3 and 4, the two approaches are compared.