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

Citation
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
Citations number
18
Categorie Soggetti
Chemistry & Analysis","Organic Chemistry/Polymer Science
Journal title
TETRAHEDRON LETTERS
ISSN journal
00404039 → ACNP
Volume
40
Issue
51
Year of publication
1999
Pages
8965 - 8968
Database
ISI
SICI code
0040-4039(199912)40:51<8965:SOEPCP>2.0.ZU;2-D
Abstract
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.