Highly efficient synthesis and stereoselective migration reactions of chiral five-membered aza-spiroindolenines: scope and mechanistic understanding

Chemical Science
Qing-Feng WuShu-Li You

Abstract

An Ir-catalyzed asymmetric synthesis of five-membered aza-spiroindolenines is achieved. Based on the detailed investigation of the reaction patterns of the aryl iminium migration, a one-pot asymmetric allylic dearomatization/migration sequence from racemic indole derivatives is realized, affording enantioenriched Pictet-Spengler-type products bearing an additional allylic stereogenic center adjacent to the C3 position of the indole core.

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Citations

Dec 7, 2018·Chemistry : a European Journal·Prabhat RanjanErik V Van der Eycken
Feb 25, 2020·Angewandte Chemie·James A Rossi-AshtonShu-Li You
Aug 29, 2017·Chemistry, an Asian Journal·Zheng-Le ZhaoShu-Li You
Mar 27, 2018·Chemical Communications : Chem Comm·Pavel FedoseevErik V Van der Eycken
Apr 2, 2021·ACS Central Science·Chao Zheng, Shu-Li You
Jan 30, 2019·Organic Letters·Dhanarajan Arunprasath, Govindasamy Sekar
Sep 15, 2020·The Journal of Organic Chemistry·Lance T Lepovitz, Stephen F Martin
Aug 24, 2021·Organic Letters·Dimitrios AndreouIoannis N Lykakis
May 31, 2018·The Journal of Organic Chemistry·Abhijeet S JadhavRamasamy Vijaya Anand
May 11, 2018·Organic Letters·John T R LiddonWilliam P Unsworth
Dec 16, 2016·Journal of the American Chemical Society·Xingyu JiangJohn F Hartwig
Dec 26, 2018·Chemical Reviews·Qiang ChengShu-Li You

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Methods Mentioned

BETA
X-ray

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