Diastereoselective synthesis of trans-N-benzyl-2-(2-methylphenyl)-6-phenyl-4-piperidone

Authors
Ishimaru, K Kojima, T
Citation
K. Ishimaru et T. Kojima, Diastereoselective synthesis of trans-N-benzyl-2-(2-methylphenyl)-6-phenyl-4-piperidone, HETEROCYCLE, 55(8), 2001, pp. 1591-1597
Citations number
23
Categorie Soggetti
Organic Chemistry/Polymer Science
Journal title
HETEROCYCLES
ISSN journal
03855414 → ACNP
Volume
55
Issue
8
Year of publication
2001
Pages
1591 - 1597
Database
ISI
SICI code
0385-5414(20010801)55:8<1591:DSOT>2.0.ZU;2-U
Abstract
Diastereoselective synthesis of trans-N-benzyl-2-(2-methylphenyl)-6-phenyl- 4-piperidone (6a) was performed by cycloaddition of the aldimine (1c) with 2-silyloxy-1,3-butadiene in the presence of trimethylsilyl triflate. The us e of the p-trimethylsilyl substituent of the aromatic ring of the aldimine gave high diastereoselectivity of the product.