One-pot transformation of p-toluenesulfonates of 2,3-epoxy alcohols into allyic alcohols

✍ Scribed by Hiromu Habashita; Takeshi Kawasaki; Masako Akaji; Hirokazu Tamamura; Tetsutaro Kimachi; Nobutaka Fujii; Toshiro Ibuka

• Book ID: 104258279
• Publisher: Elsevier Science
• Year: 1997
• Tongue: French
• Weight: 255 KB
• Volume: 38
• Category: Article
• ISSN: 0040-4039
• DOI: 10.1016/s0040-4039(97)10208-8

✦ Synopsis

A convenient and efficient method for the synthesis of synthetically useful non-racemic allylic alcohols from 4-methylbenzenesulfonates of non-racemic 2,3-epoxy alcohols is described. Satisfactory yields are obtained by treatment of 4-methylbenzenesulfonates of non-racemic 2,3-epoxy alcohols with potassium iodide followed by zinc powder and ammonium chloride in a one-pot manner. The method has been successfully applied to the synthesis of a key building block of C30-C37 botryococcenes.