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Tian D, Li C, Gu G, et al. Stereospecific Nucleophilic Substitution with Arylboronic Acids as Nucleophiles in the Presence of a CONH Group. Angew Chem Int Ed Engl. 2018;57(24):7176-7180doi: 10.1002/anie.201712829.
Tian, D., Li, C., Gu, G., Peng, H., Zhang, X., & Tang, W. (2018). Stereospecific Nucleophilic Substitution with Arylboronic Acids as Nucleophiles in the Presence of a CONH Group. Angewandte Chemie (International ed. in English), 57(24), 7176-7180. https://doi.org/10.1002/anie.201712829
Tian, Duanshuai, et al. "Stereospecific Nucleophilic Substitution with Arylboronic Acids as Nucleophiles in the Presence of a CONH Group." Angewandte Chemie (International ed. in English) vol. 57,24 (2018): 7176-7180. doi: https://doi.org/10.1002/anie.201712829
Tian D, Li C, Gu G, Peng H, Zhang X, Tang W. Stereospecific Nucleophilic Substitution with Arylboronic Acids as Nucleophiles in the Presence of a CONH Group. Angew Chem Int Ed Engl. 2018 Jun 11;57(24):7176-7180. doi: 10.1002/anie.201712829. Epub 2018 May 09. PMID: 29687594.
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Angew Chem Int Ed Engl. 2018 Jun 11;57(24):7176-7180. doi: 10.1002/anie.201712829. Epub 2018 May 09.

Stereospecific Nucleophilic Substitution with Arylboronic Acids as Nucleophiles in the Presence of a CONH Group.

Angewandte Chemie (International ed. in English)

Duanshuai Tian, Chengxi Li, Guoxian Gu, Henian Peng, Xumu Zhang, Wenjun Tang

Affiliations

  1. State Key Laboratory of Bio-Organic and Natural Products Chemistry, Center for Excellence in Molecular Synthesis, Shanghai Institute of Organic Chemistry, University of Chinese Academy of Sciences, 345 Ling Ling Rd, Shanghai, 200032, P. R. China.
  2. Department of Chemistry, South University of Science and Technology of China, Shenzhen, 518055, P. R. China.

PMID: 29687594 DOI: 10.1002/anie.201712829

Abstract

Stereospecific nucleophilic substitution was achieved for the first time with arylboronic acids as nucleophiles. This transition-metal-free coupling between chiral α-aryl-α-mesylated acetamides and arylboronic acids provided access to a series of chiral α,α-diaryl acetamides with excellent enantioselectivity and moderate to good yields. The CONH functionality proved to be crucial for bridging the reactants and promoting the reaction. Efficient syntheses of a cannabinoid CB

© 2018 Wiley-VCH Verlag GmbH & Co. KGaA, Weinheim.

Keywords: arylboronic acids; enantioselectivity; nucleophilic substitution; stereospecificity; α,α-diaryl acetamides

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