Practical Synthesis of (S)‐(+)‐3‐Octanol by Lipase‐Catalyzed Enantioselective Acetylation

Abstract

(S)‐(+)‐3‐Octanol (S)‐1 was prepared in high enantiomeric excess through catalyzed acetylation of racemic alcohol 1 by using lipase from Candida antarctica (Chirazyme L‐2) in the presence of vinyl acetate in toluene at 30°C. The pure (S)‐1 was obtained in 73% isolated yield with 62% conversion. Moreover, acetate (R)‐2 was converted to (S)‐1 via mesylation and followed by hydrolysis using sodium bicarbonate solution in 44% yield.

Keywords:

• Candida antarctica
• enantioselective acetylation
• inversion
• lipase
• (R)‐(+)‐1‐ethylhexyl acetate, (S)‐(+)‐3‐Octonol