Process for synthesis of chiral cis- and trans-3-amino-4-substituted pyrrolidine compounds

Process for preparation of chiral cis-3,4-substituted pyrrolidine compounds having the formulas and chiral 3,4-trans-substituted pyrrolidine compounds having the formulas with the assistance of a stereochemically directing chiral oxazolidinone moiety having the formula wherein P, R and R1 are specifically defined, by sequential reaction of the compound or subsequent intermediates with an a,b-unsaturated acid chloride, reaction with N-benzyl-N-(methoxymethyl)trimethylsilylmethylamine and separating isomers by chromatography, hydrolytic removal of the oxazolidinone moiety, reaction with diphenylphosphoryl azide and triethylamine, and debenzylating; and novel intermediates of the process. Process for preparation of chiral cis-3,4-substituted pyrrolidine compounds having the formulas and chiral 3,4-trans-substituted pyrrolidine compounds having the formulas with the assistance of a stereochemically directing chiral oxazolidinone moiety having the formula wherein P, R and R1 are specifically defined, by sequential reaction of the compound or subsequent intermediates with an a,b-unsaturated acid chloride, reaction with N-benzyl-N-(methoxymethyl)trimethylsilylmethylamine and separating isomers by chromatography, hydrolytic removal of the oxazolidinone moiety, reaction with diphenylphosphoryl azide and triethylamine, and debenzylating; and novel intermediates of the process.