A unique case of face diastereoselectivity in the Michael addition reactions between Ni(II)-complexes of glycine and chiral 3-(E-enoyl)-1,3-oxazolidin-2-ones

✍ Scribed by Vadim A Soloshonok*; Chaozhong Cai; Victor J Hruby

• Publisher: Elsevier Science
• Year: 2000
• Tongue: French
• Weight: 72 KB
• Volume: 41
• Category: Article
• ISSN: 0040-4039
• DOI: 10.1016/s0040-4039(00)01737-8

✦ Synopsis

The origin of virtually complete face diastereoselectivity in the organic base-catalyzed, room temperature Michael addition reactions between Ni(II)-complexes of Schiff bases of glycine and chiral 3-(Eenoyl)-4-substituted-1,3-oxazolidin-2-ones was shown to stem from the unusual mode of steric interactions in determining the corresponding transition state.