Stereohomogeneous synthesis of (E)- and (Z)-crotyltrifluorosilanes and highly stereoselective allylation of aldehydes

✍ Scribed by Mitsuo Kira; Takakazu Hino; Hideki Sakurai

• Book ID: 104232813
• Publisher: Elsevier Science
• Year: 1989
• Tongue: French
• Weight: 286 KB
• Volume: 30
• Category: Article
• ISSN: 0040-4039
• DOI: 10.1016/s0040-4039(01)80370-1

✦ Synopsis

Stereohomogeneous (E)-and (Z) -crotyltrifluorosilanes were prepared and used for the highly diastereoselective synthesis of threo-and erythro-/?-methylhomoallyl alcohols, respectively, from aldehydes in the presence of fluoride ions. The mechanism of the reaction was discussed.

Recently, we have reported that allyltrifluorosilanes react with various aldehydes chemoselectively in the presence of fluoride ions to give the corresponding homoallyl alcohols