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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.
Original language | English |
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Journal | Angewandte Chemie International Edition |
Volume | In press |
Early online date | 1 Aug 2018 |
DOIs | |
Publication status | E-pub ahead of print - 1 Aug 2018 |
Keywords
- Asymmetric catalysis
- Brønsted acid
- DFT
- Heterocycles
- Stereochemistry
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Dive into the research topics of 'Catalytic enantioselective synthesis of α-chiral azaheteroaryl ethylamines by asymmetric protonation'. Together they form a unique fingerprint.Projects
- 1 Finished
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Amine Catalysis: Can amine catalysis generate synthetically useful carbenes
Watson, A. J. B. (PI)
1/01/18 → 30/04/18
Project: Standard
Datasets
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Catalytic enantioselective synthesis of α-chiral azaheteroaryl ethylamines by asymmetric protonation (dataset)
Xu, C. (Creator), Muir, C. (Creator), Leach, A. (Creator), Kennedy, A. (Creator) & Watson, A. J. B. (Creator), Cambridge Crystallographic Data Centre, 2018
https://dx.doi.org/10.5517/ccdc.csd.cc1zn0j5
Dataset