Zirconium-mediated asymmetric Baeyer-Villiger oxidation

✍ Scribed by Carsten Bolm; Oliver Beckmann

• Publisher: John Wiley and Sons
• Year: 2000
• Tongue: English
• Weight: 87 KB
• Volume: 12
• Category: Article
• ISSN: 0899-0042
• DOI: 10.1002/(sici)1520-636x(2000)12:5/6<523::aid-chir39>3.0.co;2-z

✦ Synopsis

Combinations of axially chiral C2-symmetric diols were used as ligands in zirconium-mediated Baeyer-Villiger reactions. The in situ preformed Zr-diol species proved effective in the asymmetric oxidation of bicyclic and monosubstituted cyclobutanones when a hydroperoxide was employed as oxidant. Asymmetric induction could be preserved upon replacement of one out of two enantiopure BINOL ligands by conformationally flexible 2,2'-biphenol.