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
DOI:——
日期:——
A Cascade Aza-Cope/Aza-Prins Cyclization Leading to Piperidine Derivatives
作者:Jothi L. Nallasivam、Rodney A. Fernandes
DOI:10.1002/ejoc.201403607
日期:2015.3
The cascadeaza-Cope/aza-Prinscyclization of homoallylamines to give substituted piperidines has been explored. The use of glyoxalic acid as the carbonyl component afforded bicyclic structures as a result of the internal carboxylate anion trapping the intermediate cation. The unimolecular bis-, tris-, and tetrakis(homoallylamine)s efficiently delivered the appended bis-, tris- and tetrakis(piperidine-4-ol)s