Synthesis of enantiomerically pure cis-2,4-disubstituted piperidines: extension of chiral homoenolate alkylations toward the preparation of nitrogen heterocycles
Mp. Dwyer et al., Synthesis of enantiomerically pure cis-2,4-disubstituted piperidines: extension of chiral homoenolate alkylations toward the preparation of nitrogen heterocycles, TETRAHEDR L, 40(51), 1999, pp. 8965-8968
Enantiomerically pure cis-2,4-disubstituted piperidines were synthesized fr
om chiral thiolactam 2 in six steps via a highly diastereoselective homoeno
late alkylation which set the stereochemistry at the C4 carbon. In addition
, two cleavage methods were used to cleave the lactam to the desired piperi
dines with a high level of diastereoselection at the newly created C2 stere
ocenter. (C) 1999 Published by Elsevier Science Ltd. All rights reserved.