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

• Published in: Tetrahedron letters 1999-12, Vol.40 (51), p.8965-8968
• Main Authors: Dwyer, Michael P., Lamar, Jason E., Meyers, A.I.
• Format: Article
• Language: English
• ISSN: 0040-4039; 1873-3581
• 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. Enantiomerically pure cis-2,4-disubstituted piperidines were synthesized from chiral thiolactam 2 in 6 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.