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

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

Author information

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.

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

PMID:
27321285
DOI:
10.1002/chem.201602691

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