Palladium-Catalyzed Ring Expansion of Spirocyclopropanes to Form Caprolactams and Azepanes

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• 作者：Olivier Ren茅 ; Iain A. Stepek ; Alberto Gobbi ; Benjamin P. Fauber ; Simon Gaines
• 刊名：Journal of Organic Chemistry
• 出版年：2015
• 出版时间：October 16, 2015
• 年：2015
• 卷：80
• 期：20
• 页码：10218-10225
• 全文大小：461K
• ISSN：1520-6904

文摘

A palladium(0)-catalyzed rearrangement of piperidones and piperidines bearing a spirocyclopropane ring was developed. The ring expansion reaction led to a variety of functionalized caprolactam and azepane products in good to excellent yields. Experimental and computational mechanistic studies revealed an initial oxidative addition of the distal carbon鈥揷arbon bond of a cyclopropane ring to the palladium(0) catalyst and the relief of ring strain as a driving force for product formation.