Synthesis of optically active partly gem-difluorinated allylic alcohols via [2,3]-Wittig rearrangements and lipase-catalyzed reaction

✍ Scribed by Toshiyuki Itoh; Kazutoshi Kudo; Naoko Tanaka; Kohei Sakabe; Yumiko Takagi; Hiroshi Kihara

• Publisher: Elsevier Science
• Year: 2000
• Tongue: French
• Weight: 201 KB
• Volume: 41
• Category: Article
• ISSN: 0040-4039
• DOI: 10.1016/s0040-4039(00)00640-7

✦ Synopsis

2,3]-Wittig rearrangement of 1,1,2-tri¯uoroallylic ethers gave ®ve types of novel 4,4,5-tri¯uoroalk-1,5dien-3-ols. The rearrangement reaction gave the alcohols with perfect (E)*-selection over the newly created ole®n bond for two substrates. Lipase-catalyzed optical resolution of 4,4,5-tri¯uoroalk-1,5-dien-3-ols was successfully performed to aord optically active partly gem-di¯uorinated allylic alcohols for the ®rst time.