SELENIUM INDUCED STEREOSELECTIVE CYCLIZATION OF N-SUBSTITUTED-4-HYDROXY-5-HEXENYLAMINES

Authors
COOPER MA WARD AD
Citation
Ma. Cooper et Ad. Ward, SELENIUM INDUCED STEREOSELECTIVE CYCLIZATION OF N-SUBSTITUTED-4-HYDROXY-5-HEXENYLAMINES, Tetrahedron letters, 35(28), 1994, pp. 5065-5068
Citations number
15
Categorie Soggetti
Chemistry Inorganic & Nuclear
Journal title
Tetrahedron letters → ACNP
ISSN journal
00404039
Volume
35
Issue
28
Year of publication
1994
Pages
5065 - 5068
Database
ISI
SICI code
0040-4039(1994)35:28<5065:SISCON>2.0.ZU;2-X
Abstract
The selenium induced cyclization of N-substituted 4-hydroxy-5-hexenyla mines occurs regio- and stereoselectively to give N-substituted trans- 2-(phenylselenomethyl)-3-hydroxypiperidines in moderate yield. Synthes is of the biologically active diol (8) was achieved via oxidation of t he phenylseleno moiety to the phenylselenone and subsequent displaceme nt with sodium hydroxide.