The stereocontrolled formation of cyclic vicinal cis-diols via a samarium diiodide pinacol coupling of dialdehydes

✍ Scribed by Jose Luis Chiara; Walter Cabri; Stephen Hanessian

• Book ID: 104225024
• Publisher: Elsevier Science
• Year: 1991
• Tongue: French
• Weight: 309 KB
• Volume: 32
• Category: Article
• ISSN: 0040-4039
• DOI: 10.1016/s0040-4039(00)92024-0

✦ Synopsis

Aliphatic 1,5-and 1,6 dialdehydes with and without a-substituents, as well as derivatives of carbohydrate dialdehydes undergo a pinacol coupling reaction in the presence of SmI;! to give cis-diols as the preponderant products. When cc-alkoxy groups are present, the diol has an orientation that is opposite to such groups.