Asymmetric 1,3-dipolar cycloadditions of a chiral non-racemic azomethine imine

✍ Scribed by Fanny Roussi; Martine Bonin; Angèle Chiaroni; Laurent Micouin; Claude Riche; Henri-Philippe Husson

• Publisher: Elsevier Science
• Year: 1999
• Tongue: French
• Weight: 219 KB
• Volume: 40
• Category: Article
• ISSN: 0040-4039
• DOI: 10.1016/s0040-4039(99)00610-3

✦ Synopsis

Chiral non racemic carbazate 1, derived from (R)-(-)-phenylglycinol, reacts regioselectively with benzaldehyde or its dimethylacetal to give an azomethine imine. The faci~d, endo/exo and regio selectivities of 1,3-dipolar cycloadditions of this reactive species with various dipolarophiles have been studied and are described in this paper. In the best cases, up to three contiguous asymmetric centers could be generated simultaneously, in a complete enantio-and diastereoselective fashion.