Palladium(0)-Catalyzed Intermolecular Allylic Dearomatization of Indoles by a Formal [4+2] Cycloaddition Reaction

Run-Duo Gao; Qing-Long Xu; Bo Zhang; Yiting Gu; Li-Xin Dai; Shu-Li You

doi:10.1002/chem.201602691

Palladium(0)-Catalyzed Intermolecular Allylic Dearomatization of Indoles by a Formal [4+2] Cycloaddition Reaction

Chemistry. 2016 Aug 8;22(33):11601-4. doi: 10.1002/chem.201602691. Epub 2016 Jul 14.

Authors

Run-Duo Gao¹, Qing-Long Xu¹, Bo Zhang¹, Yiting Gu¹, Li-Xin Dai¹, Shu-Li You^{2

3}

Affiliations

¹ State Key Laboratory of Organometallic Chemistry, Shanghai Institute of Organic Chemistry, Chinese Academy of Sciences, 345 Lingling Lu, Shanghai, 200032, P. R. China.
² State Key Laboratory of Organometallic Chemistry, Shanghai Institute of Organic Chemistry, Chinese Academy of Sciences, 345 Lingling Lu, Shanghai, 200032, P. R. China. slyou@sioc.ac.cn.
³ Collaborative Innovation Center of Chemical Science and Engineering, Tianjin, 300072, P. R. China. slyou@sioc.ac.cn.

PMID: 27321285
DOI: 10.1002/chem.201602691

Abstract

Bridged indoline derivatives were synthesized by an intermolecular Pd-catalyzed allylic dearomatization reaction of substituted indoles. The reaction between indoles and allyl carbonates bearing a nucleophilic alcohol side-chain proceeds in a cascade fashion, providing bridged indolines in excellent enantioselectivity.

Keywords: asymmetric catalysis; dearomatization; indole; indoline; palladium.