Stereochemistry of the glyoxylate N-sulfonylimine ene reaction

✍ Scribed by David M. Tschaen; Steven M. Weinreb

• Book ID: 104220992
• Publisher: Elsevier Science
• Year: 1982
• Tongue: French
• Weight: 194 KB
• Volume: 23
• Category: Article
• ISSN: 0040-4039
• DOI: 10.1016/s0040-4039(00)87521-8

✦ Synopsis

Ene reactions of sulfonylimine J& with cyclohexene and trans-2-butene are highly stereoselective, affording products 2 and l0, respectively.

Recently, Achmatowicz reported that N-toluenesulfonylimine & derived from n-butyl glyoxylate undergoes facile ene reactions thermally or under Lewis acid catalysis to afford y,6unsaturated-cr-amino acid derivatives 1.1 This reaction appears to offer a potentially efficient route to a variety of complex natural products containing amino acid functionality. 2