Chromium-Catalyzed Asymmetric Dearomatization–Addition Reactions of Halomethyloxazoles and Indoles

Zheng Wang; Hongtao Ji; Wei-Min He; Yang Xiong; Guozhu Zhang

doi:10.1055/s-0037-1609753

Synthesis, Inhaltsverzeichnis

Synthesis 2018; 50(24): 4915-4921
DOI: 10.1055/s-0037-1609753

paper

Chromium-Catalyzed Asymmetric Dearomatization–Addition Reactions of Halomethyloxazoles and Indoles

Zheng Wang

^aHunan Provincial Engineering Research Center for Ginkgobiloba, Hunan University of Science and Engineering, 130 Yangzi Tan Road, Yongzhou 425100, P. R. of China eMail: weiminhe2016@yeah.net

,

Hongtao Ji

^aHunan Provincial Engineering Research Center for Ginkgobiloba, Hunan University of Science and Engineering, 130 Yangzi Tan Road, Yongzhou 425100, P. R. of China eMail: weiminhe2016@yeah.net

,

Wei-Min He *

^aHunan Provincial Engineering Research Center for Ginkgobiloba, Hunan University of Science and Engineering, 130 Yangzi Tan Road, Yongzhou 425100, P. R. of China eMail: weiminhe2016@yeah.net

,

Yang Xiong

^bState Key Laboratory of Organometallic Chemistry, Shanghai Institute of Organic Chemistry, Center for Excellence in Molecular Synthesis, Chinese Academy of Sciences, 345 Lingling Road, Shanghai 200032, P. R. of China eMail: guozhuzhang@sioc.ac.cn

,

Guozhu Zhang *

^bState Key Laboratory of Organometallic Chemistry, Shanghai Institute of Organic Chemistry, Center for Excellence in Molecular Synthesis, Chinese Academy of Sciences, 345 Lingling Road, Shanghai 200032, P. R. of China eMail: guozhuzhang@sioc.ac.cn

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Abstract

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Abstract

The asymmetric dearomatization–addition reaction of halomethyloxazoles and halomethylindoles with aldehydes is realized in the presence of a carbazole-based bisoxazoline CrCl₂ complex to afford the corresponding enantioenriched, hydroxylated oxazoline and indoline products. The observed excellent chemo-, regio-, diastereo- and enantioselectivities are notable advantages of this protocol. The strategy established in this study is expected to find application in the synthesis of azaheterocycles with biological significance and useful functionalities.

Key words

asymmetric–dearomatization - chromium catalysis - oxazolines - indolines - azaheterocycles

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Referenzen

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