Stereoselective synthesis of 26-disubstituted piperidine alkaloids via TiCl4 induced iminium ion cyclization of α-cyanoamines

✍ Scribed by Teng-Kuei Yang; Tsung-Fan Teng; Jyh-Hwa Lin; Yen-Yuan Lay

• Publisher: Elsevier Science
• Year: 1994
• Tongue: French
• Weight: 155 KB
• Volume: 35
• Category: Article
• ISSN: 0040-4039
• DOI: 10.1016/s0040-4039(00)73244-8

✦ Synopsis

The stereoselective cyclixation of an a-cyanoamine containing a vinyl group induced by Tic4 in a methylene chloride solution, produces cis 2,6-dialkylpiperidine; whereas a similar reaction of an acyanoamine containing a silyl substituted vinyl group gave the corresponding tram isomer only.

The piperidine ring is one of the most abundant skeleton in the naturally occurring alkaloids. With proper