尾-Olefination of 2-Alkynoates Leading to Trisubstituted 1,3-Dienes

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• 作者：Mathias J. Jacobsen ; Erik Daa Funder ; Jacob R. Cramer ; Kurt V. Gothelf
• 刊名：Organic Letters
• 出版年：2011
• 出版时间：July 1, 2011
• 年：2011
• 卷：13
• 期：13
• 页码：3418-3421
• 全文大小：750K
• 年卷期：v.13,no.13(July 1, 2011)
• ISSN：1523-7052

文摘

A phosphine-mediated olefination of 2-alkynoates with aldehydes forming 1,3-dienes with high E-selectivity and up to 88% yield is described. Reaction conditions are optimized and reactions are demonstrated for various aryl, alkyl, and alkenyl aldehydes and for ethyl 2-alkynoates with different substituents in the 未-position. Proof of concept is shown for the generation of a 尾,纬-unsaturated lactone by intramolecular olefination, and furthermore the use of the generated 1,3-dienes in the Diels鈥揂lder reaction has been demonstrated.