Ma. Cooper et Ad. Ward, SELENIUM INDUCED STEREOSELECTIVE CYCLIZATION OF N-SUBSTITUTED-4-HYDROXY-5-HEXENYLAMINES, Tetrahedron letters, 35(28), 1994, pp. 5065-5068
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.