Pd-Catalyzed Regioselective and Stereospecific Suzuki鈥揗iyaura Coupling of Allylic Carbonates with Arylboronic Acids

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• 作者：Chenguang Li ; Juxiang Xing ; Jingming Zhao ; Patrick Huynh ; Wanbin Zhang ; Pingkai Jiang ; Yong Jian Zhang
• 刊名：Organic Letters
• 出版年：2012
• 出版时间：January 6, 2012
• 年：2012
• 卷：14
• 期：1
• 页码：390-393
• 全文大小：289K
• 年卷期：v.14,no.1(January 6, 2012)
• ISSN：1523-7052

文摘

The Pd-catalyzed Suzuki鈥揗iyaura coupling reaction of unsymmetric 1,3-disubstituted secondary allylic carbonates with arylboronic acids has been developed in a wet solvent under a base-free system to afford allyl鈥揳ryl coupling products in a high level of isolated yields with complete regio- and E/Z-selectivities with good to excellent chemoselectivities. The coupling reaction of optically active allyl carbonates gave allyl鈥揳ryl coupling products with excellent enantioselectivities with inversion of the stereochemistry. This coupling method was successfully applied to the synthesis of (S)-naproxen.