Ring opening of DA-cyclopropanes with electron rich arene/heteroarene: synthesis of 2-(2,2-diarylethyl)malonates

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• 作者：Ranadeep Talukdar ; Amrita Saha ; Deo Prakash Tiwari ; Manas K. Ghorai ; ^{mkghorai@iitk.ac.in" class="auth_mail" title="E-mail the corresponding author}
• 关键词：2-(2 ; 2-Diarylethyl)malonates ; DA-cyclopropanes ; Nucleophilic ring opening ; Electron rich arene ; Indole
• 刊名：Tetrahedron
• 出版年：2016
• 出版时间：4 February 2016
• 年：2016
• 卷：72
• 期：5
• 页码：613-624
• 全文大小：1212 K

文摘

An efficient strategy for nucleophilic ring opening of donor-acceptor (DA)-cyclopropanes with electron rich arenes to provide 2-(2,2-diarylethyl)malonates in excellent yields is described. The reaction was found to be successful with heteroarenes as the nucleophile as well. Reaction of enantiopure DA-cyclopropane with arene/heteroarene as the nucleophiles afforded the corresponding 2-(2,2-diarylethyl)malonates with high yield and enantioselectivity (ee 95%). The synthetic utility of the products was demonstrated by converting them easily into other important synthetic scaffolds like functionalized cyclohexene and malonic acid derivatives.