One-pot sequential cross-metathesis/hydride reduction: highly stereoselective synthesis of primary (E)-allylic alcohols from terminal olefins

✍ Scribed by Tapas Paul; Gopal Sirasani; Rodrigo B. Andrade

• Publisher: Elsevier Science
• Year: 2008
• Tongue: French
• Weight: 149 KB
• Volume: 49
• Category: Article
• ISSN: 0040-4039
• DOI: 10.1016/j.tetlet.2008.03.132

✦ Synopsis

Several di-and trisubstituted primary (E)-allylic alcohols have been prepared from the corresponding terminal olefins in a highly stereoselective manner (>20:1 E/Z) by sequencing olefin cross-metathesis (CM) with hydride reduction (DIBAL-H) in good yields utilizing only commercially available reagents in a one-pot fashion. The method is a reliable alternative to the direct CM of terminal olefins with allyl alcohol, which is not always stereoselective but rather highly substrate dependent.