The stereoselective cyclization of an α-cyanoamine containing a vinyl group induced by TiCl4 in a methylene chloride solution, produces cis 2,6-dialkylpiperidine; whereas a similar reaction of an α-cyanoamine containing a silyl substituted vinyl group gave the corresponding trans isomer only.
The nucleophilic substitution by primary amines of secondary homoallylic mesylates easily obtained from corresponding alcohols offers a convenient way to prepare homoallylic amines. The relative low yields in pure compounds is counterbalanced by the simplicity of the procedure.
Henin Francoise, Mahuct Evelyne, Muller Caroline, Muzart Jacques, Synth. Commun., 25 (1995) N 9, S 1331-1338
作者:Henin Francoise, Mahuct Evelyne, Muller Caroline, Muzart Jacques