Organocatalytic discrimination of non-directing aryl and heteroaryl groups: enantioselective synthesis of bioactive indole-containing triarylmethanes

Author:

Yan Qiaolin1,Duan Meng23,Chen Cien45,Deng Zhiqing56ORCID,Wu Mandi45,Yu Peiyuan3ORCID,He Ming-Liang45ORCID,Zhu Guangyu56ORCID,Houk K. N.2ORCID,Sun Jianwei17ORCID

Affiliation:

1. Department of Chemistry, the Hong Kong Branch of Chinese National Engineering Research Centre for Tissue Restoration & Reconstruction, The Hong Kong University of Science and Technology (HKUST), Clear Water Bay, Kowloon, Hong Kong SAR, China

2. Department of Chemistry and Biochemistry, University of California, Los Angeles, California 90095, USA

3. Department of Chemistry and Shenzhen Grubbs Institute, Guangdong Provincial Key Laboratory of Catalysis, Southern University of Science and Technology, Shenzhen, 518055, China

4. Department of Biomedical Sciences, City University of Hong Kong, Kowloon Tong, Hong Kong SAR, China,

5. CityU Shenzhen Research Institute, Shenzhen, China

6. Department of Chemistry, City University of Hong Kong, Kowloon Tong, Hong Kong SAR, China

7. Shenzhen Research Institute, HKUST, No. 9 Yuexing 1st Rd, Shenzhen 518057, China

Abstract

Excellent enantiodiscrimination between aryl and heteroaryl groups without a directing group has been achieved with organocatalysis. The highly enantioenriched triarylmethane products exhibit anticancer and antiviral activities.

Funder

Guangdong Provincial Key Laboratory of Catalysis

National Science Foundation

National Natural Science Foundation of China

Research Grants Council, University Grants Committee

Science, Technology and Innovation Commission of Shenzhen Municipality

Publisher

Royal Society of Chemistry (RSC)

Subject

General Chemistry

Reference55 articles.

1. E. N.Jacobsen , A.Pfaltz and H.Yamamoto , Comprehensive Asymmetric Catalysis I–III , Springer , Berlin , 1999

2. P. J.Walsh and M. C.Kozlowski , Fundamentals of Asymmetric Catalysis , University Science Books , Sausalito, CA , 2008

3. E. M.Carreira and H.Yamamoto , Comprehensive Chirality , 1st edn, Elsevier Science , 2012

4. H. U.Blaser and H.-J.Federsel , Asymmetric Catalysis on Industrial Scale: Challenges, Approaches, and Solutions , Wiley-VCH , 2010

5. Chiral 1,1-diaryl compounds as important pharmacophores

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