Lewis acid-catalyzed intramolecular asymmetric ene reactions of chiral vinyl sulfoxide

✍ Scribed by Kunio Hiroi; Masayuki Umemura

• Publisher: Elsevier Science
• Year: 1992
• Tongue: French
• Weight: 233 KB
• Volume: 33
• Category: Article
• ISSN: 0040-4039
• DOI: 10.1016/s0040-4039(00)92084-7

✦ Synopsis

Ablracf: A chid a-cyanovinyl sulfoxide served as an efficient chiral enophile in a Lewis acid-catalyzed intramolecular ene reaction. Use of diethylaluminum chloride as a catalyst provided extremely high stereoselectivity in this ene reaction. Based on the stereochemical results obtained, a mechanistic pathway for this asymmetric induction is presented.

An ene reaction is one of the useful tools for stereoselective construction of complex molecu1es.l) Especially