Synthesis 2018; 50(24): 4915-4921
DOI: 10.1055/s-0037-1609753
paper
© Georg Thieme Verlag Stuttgart · New York

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

Zheng Wang
a  Hunan 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
a  Hunan 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
,
a  Hunan 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
b  State 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
,
b  State 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
› Author Affiliations
We are grateful to NSFC-21772218, 21421091, XDB20000000, the ‘Thousand Plan’ Youth program, State Key Laboratory of Organometallic Chemistry, Shanghai Institute of Organic Chemistry, Chinese Academy of Sciences, the Science and Technology Innovative Research Team in Higher Educational Institutions of Hunan Province (2012-318) and the Construct Program of the Key Discipline in Hunan Province.
Further Information

Publication History

Received: 06 February 2018

Accepted after revision: 09 April 2018

Publication Date:
29 May 2018 (online)

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.

Supporting Information

 
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