Switchover of diastereofacial selectivity in the condensation reaction of optically active N-sulfinimine with ester enolate

Article abstract of DOI:10.1016/0040-4039(96)00707-1

Both diastereomers of β-aminoester can be obtained diastereoselectively in the reaction of optically active N-sulfinimine possessing 2-methyl-1,3- dioxolanyl group with ester enolate simply by changing the enolate metal species, additives, and solvents. The β-aminoester can be converted into the corresponding 3-unsubstituted β-lactam.