Stereoselective Synthesis of Nipecotic Acid Derivatives via Palladium-Catalyzed Decarboxylative Cyclization of γ-Methylidene-δ-valerolactones with Imines

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• 作者：Ryo Shintani ; Masataka Murakami ; Tamio Hayashi
• 刊名：Organic Letters
• 出版年：2009
• 出版时间：January 15, 2009
• 年：2009
• 卷：11
• 期：2
• 页码：457-459
• 全文大小：155K
• 年卷期：v.11,no.2(January 15, 2009)
• ISSN：1523-7052

文摘

A new synthetic method of multisubstituted nipecotic acid (piperidine-3-carboxylic acid) derivatives has been developed by way of palladium-catalyzed decarboxylative cyclization of γ-methylidene-δ-valerolactones with imines. By employing the diethoxyphosphinoyl group as the N-protecting group for imines, the reaction proceeds smoothly with high diastereoselectivity. The products thus obtained can be further derivatized with high efficiency under simple reaction conditions.