Selenium induced stereoselective cyclization of N-protected 3-hydroxy-4-pentenylamines

Article abstract of DOI:10.1016/S0040-4039(00)61110-3

The selenium induced cyclofunctionalization of N-protected 3-hydroxy-4-pentenylamine occurs regio-and steroselectively to give N-protected cis-2-(selenomethyl)-3-hydroxypyrrolidines in high yield. The rate of reaction and degree of stereo selectivity is shown to be dependent on the nature of the selenium reagent, reaction temperature and solvent.