Synthesis of enantiomerically pure cis-2,4-disubstituted piperidines: Extension of chiral homoenolate alkylations toward the preparation of nitrogen heterocycles

Article abstract of DOI:10.1016/S0040-4039(99)01784-0

Enantiomerically pure cis-2,4-disubstituted piperidines were synthesized from chiral thiolactam 2 in six steps via a highly diastereoselective homoenolate alkylation which set the stereochemistry at the C4 carbon. In addition, two cleavage methods were used to cleave the lactam to the desired piperidines with a high level of diastereoselection at the newly created C2 stereocenter.