Catalyst-Free Synthesis of Skipped Dienes from Phosphorus Ylides, Allylic Carbonates, and Aldehydes via a One-Pot SN2鈥?Allylation鈥揥ittig Strategy

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• 作者：Silong Xu ; Shaoying Zhu ; Jian Shang ; Junjie Zhang ; Yuhai Tang ; Jianwei Dou
• 刊名：Journal of Organic Chemistry
• 出版年：2014
• 出版时间：April 18, 2014
• 年：2014
• 卷：79
• 期：8
• 页码：3696-3703
• 全文大小：342K
• 年卷期：v.79,no.8(April 18, 2014)
• ISSN：1520-6904

文摘

A catalyst-free allylic alkylation of stabilized phosphorus ylides with allylic carbonates via a regioselective S_N2鈥?process is presented. Subsequent one-pot Wittig reaction with both aliphatic and aromatic aldehydes as well as ketenes provides structurally diverse skipped dienes (1,4-dienes) in generally high yields and moderate to excellent stereoselectivity with flexible substituent patterns. This one-pot S_N2鈥?allylation鈥揥ittig strategy constitutes a convenient and efficient synthetic method for highly functionalized skipped dienes from readily available starting materials.