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

Xu, C, Muir, CW, Leach, AG, Kennedy, AR and Watson, AJB (2018) Catalytic Enantioselective Synthesis of α-Chiral Azaheteroaryl Ethylamines by Asymmetric Protonation. Angewandte Chemie International Edition. ISSN 1521-3773

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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.

Item Type: Article
Uncontrolled Keywords: 03 Chemical Sciences
Subjects: Q Science > QD Chemistry
R Medicine > RM Therapeutics. Pharmacology
Divisions: Pharmacy & Biomolecular Sciences
Publisher: Wiley
Related URLs:
Date Deposited: 14 Aug 2018 10:45
Last Modified: 30 Sep 2018 14:54
DOI or Identification number: 10.1002/anie.201806956
URI: http://researchonline.ljmu.ac.uk/id/eprint/9088

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