Rhodium(II)-Catalyzed Enantioselective C鈭扝 Functionalization of Indoles

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• 作者：Andrew DeAngelis ; Valerie W. Shurtleff ; Olga Dmitrenko ; Joseph M. Fox
• 刊名：Journal of the American Chemical Society
• 出版年：2011
• 出版时间：February 16, 2011
• 年：2011
• 卷：133
• 期：6
• 页码：1650-1653
• 全文大小：869K
• 年卷期：v.133,no.6(February 16, 2011)
• ISSN：1520-5126

文摘

A catalytic, enantioselective method for the C鈭扝 functionalization of indoles by diazo compounds has been achieved. With catalytic amounts of Rh₂(S-NTTL)₄, the putative Rh鈭抍arbene intermediates from 伪-alkyl-伪-diazoesters react with indoles at C(3) to provide 伪-alkyl-伪-indolylacetates in high yield and enantioselectivity. From DFT calculations, a mechanism is proposed that involves a Rh鈭抷lide intermediate with oxocarbenium character.