Asymmetric Baeyer-Villiger reaction: Diastereodifferentiating peracid oxidation of chiral acetal in the presence of Lewis acid

✍ Scribed by Takashi Sugimura; Yoshihisa Fujiwara; Akira Tai

• Publisher: Elsevier Science
• Year: 1997
• Tongue: French
• Weight: 227 KB
• Volume: 38
• Category: Article
• ISSN: 0040-4039
• DOI: 10.1016/s0040-4039(97)01338-5

✦ Synopsis

Oxidation of 2 with m-chloroperbenzoic acid in the presence of SnCI4 at -78 °C followed by hydrolysis afforded optically active 4 in a quantitative yield. The enantiomeric excess (ee) of 4 largely depended on the reaction solvent, the chiral diol part, the Lewis acid and its amount. The best ee was 89% when 2 (R = Ph) having 2,4-pentanediol was oxidized at -100 °C.