Phosphine-Catalyzed Synthesis of 3,3-Spirocyclopenteneoxindoles from 纬-Substituted Allenoates: Systematic Studies and Targeted Applications

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• 作者：Catherine Gomez ; Maxime Gicquel ; Jean-Christophe Carry ; Laurent Schio ; Pascal Retailleau ; Arnaud Voituriez ; Angela Marinetti
• 刊名：The Journal of Organic Chemistry
• 出版年：2013
• 出版时间：February 15, 2013
• 年：2013
• 卷：78
• 期：4
• 页码：1488-1496
• 全文大小：396K
• 年卷期：v.78,no.4(February 15, 2013)
• ISSN：1520-6904

文摘

The phosphine-promoted [3 + 2] cyclizations between 纬-substituted allenoates and arylideneoxindoles have been applied to the stereoselective synthesis of spiro(cyclopentene)oxindoles with trisubstituted cyclopentene units. It has been demonstrated that PPh₃ operates a very efficient control of the relative stereochemistry of the three stereogenic centers of the final spiranic products. Focused experiments have been carried out then so as to access carbocyclic analogues of an important series of anticancer agents inhibiting MDM2-p53 interactions.