Gold-catalyzed ring expansions of 1-alkynylcyclobutanol derivatives via tandem hydration and -ketol rearrangement

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• 作者：Ki-Dae Kim ; Hyun-Suk Yeom ; Sunwoong Shin ; Seunghoon Shin ; ^{sshin@hanyang.ac.kr}
• 关键词：Gold catalysis ; ¦Á-Ketol rearrangement ; Ring expansion ; Tandem reaction ; ¦Á-Hydroxycyclopentanone
• 刊名：Tetrahedron
• 出版年：2012
• 出版时间：1 July, 2012
• 年：2012
• 卷：68
• 期：26
• 页码：5241-5247
• 全文大小：1094 K

文摘

We report herein the gold-catalyzed tandem hydration/-ketol rearrangement of 1-alkynylcyclobutanol derivatives, leading to cyclopentanones bearing an -hydroxy substituted quaternary center. In the presence of water, coordination of gold catalyst onto alkynyl moiety triggers hydration rather than a direct ring expansion, which followed by unprecedented Au-catalyzed -ketol rearrangement. The details and the scope of this method are presented.