A convenient new method to construct 1-alkynyl cyclopropanol and its synthetic application to prepare trisubstituted dienones

✍ Scribed by Yan An; Jie Liu; Hai-Ying Jiang; Yahui Wang; Zili Chen

• Publisher: Elsevier Science
• Year: 2008
• Tongue: French
• Weight: 151 KB
• Volume: 49
• Category: Article
• ISSN: 0040-4039
• DOI: 10.1016/j.tetlet.2008.03.041

✦ Synopsis

A new synthetic route was developed via the nucleophilic addition of lithium alkynylide to 1-arylsulfonyl cyclopropanol 1 to afford 1-alkynyl cyclopropanol, which then reacted with aryl iodide to construct trisubstituted cross-conjugated dienones through a palladiumcatalyzed process, where the key steps included the regioselective carbopalladation of arylpalladium(II) intermediate across the triple bond of 1-alkynyl cyclopropanol and the ring opening of the cyclopropyl group.