Synthesis of tertiary 1,3-butadien-2-ylcarbinols from chromium-catalyzed addition of (4-bromobut-2-ynyl)trimethylsilane to ketones

✍ Scribed by María Durán-Galván; James R. Hemmer; Brian T. Connell

• Book ID: 104098122
• Publisher: Elsevier Science
• Year: 2010
• Tongue: French
• Weight: 809 KB
• Volume: 51
• Category: Article
• ISSN: 0040-4039
• DOI: 10.1016/j.tetlet.2010.07.104

✦ Synopsis

The synthesis of 1,3-butadien-2-ylcarbinols containing a tertiary alcohol is achieved by desilylation of (trimethylsilyl)methylallenic alcohols. The latter are obtained via a chromium-catalyzed addition of (4bromobut-2-ynyl)trimethylsilane to aliphatic or aromatic ketones. The desired adducts are obtained in yields ranging from 21% to 67% for this two-step, one-pot process.