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- Title
Catalytic Enantioselective Synthesis of α‐Chiral Azaheteroaryl Ethylamines by Asymmetric Protonation.
- Authors
Xu, Chao; Muir, Calum W.; Leach, Andrew G.; Kennedy, Alan R.; Watson, Allan J. B.
- Abstract
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.
- Subjects
ENANTIOSELECTIVE catalysis; ETHYLAMINES; PROTON transfer reactions; HETEROCYCLIC compounds; PHOSPHORIC acid; AROMATIZATION catalysts
- Publication
Angewandte Chemie, 2018, Vol 130, Issue 35, p11544
- ISSN
0044-8249
- Publication type
Article
- DOI
10.1002/ange.201806956