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Xu C, Muir CW, Leach AG, et al. Catalytic Enantioselective Synthesis of α-Chiral Azaheteroaryl Ethylamines by Asymmetric Protonation. Angew Chem Int Ed Engl. 2018;57(35):11374-11377doi: 10.1002/anie.201806956.
Xu, C., Muir, C. W., Leach, A. G., Kennedy, A. R., & Watson, A. J. B. (2018). Catalytic Enantioselective Synthesis of α-Chiral Azaheteroaryl Ethylamines by Asymmetric Protonation. Angewandte Chemie (International ed. in English), 57(35), 11374-11377. https://doi.org/10.1002/anie.201806956
Xu, Chao, et al. "Catalytic Enantioselective Synthesis of α-Chiral Azaheteroaryl Ethylamines by Asymmetric Protonation." Angewandte Chemie (International ed. in English) vol. 57,35 (2018): 11374-11377. doi: https://doi.org/10.1002/anie.201806956
Xu C, Muir CW, Leach AG, Kennedy AR, Watson AJB. Catalytic Enantioselective Synthesis of α-Chiral Azaheteroaryl Ethylamines by Asymmetric Protonation. Angew Chem Int Ed Engl. 2018 Aug 27;57(35):11374-11377. doi: 10.1002/anie.201806956. Epub 2018 Aug 01. PMID: 29956430.
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Angew Chem Int Ed Engl. 2018 Aug 27;57(35):11374-11377. doi: 10.1002/anie.201806956. Epub 2018 Aug 01.

Catalytic Enantioselective Synthesis of α-Chiral Azaheteroaryl Ethylamines by Asymmetric Protonation.

Angewandte Chemie (International ed. in English)

Chao Xu, Calum W Muir, Andrew G Leach, Alan R Kennedy, Allan J B Watson

Affiliations

  1. EaStCHEM, School of Chemistry, University of St Andrews, North Haugh, St Andrews, Fife, KY16 9ST, UK.
  2. Department of Pure and Applied Chemistry, University of Strathclyde, 295 Cathedral Street, Glasgow, G1 1XL, UK.
  3. School of Pharmacy and Biomolecular Sciences, Liverpool John Moores University, Byrom Street, Liverpool, L3 3AF, UK.

PMID: 29956430 DOI: 10.1002/anie.201806956

Abstract

The direct enantioselective synthesis of chiral azaheteroaryl ethylamines from vinyl-substituted N-heterocycles and anilines is reported. A chiral phosphoric acid (CPA) catalyst promotes dearomatizing aza-Michael addition to give a prochiral exocyclic aryl enamine, which undergoes asymmetric protonation upon rearomatization. The reaction accommodates a broad range of N-heterocycles, nucleophiles, and substituents on the prochiral centre, generating the products in high enantioselectivity. DFT studies support a facile nucleophilic addition based on catalyst-induced LUMO lowering, with site-selective, rate-limiting, intramolecular asymmetric proton transfer from the ion-paired prochiral intermediate.

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

Keywords: Brønsted acids; asymmetric catalysis; heterocycles; organocatalysis; stereochemistry

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