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Asymmetric Synthesis of Hydroquinolines with α,α-Disubstitution through Organocatalyzed Kinetic Resolution.
- Source :
-
Angewandte Chemie (International ed. in English) [Angew Chem Int Ed Engl] 2021 Mar 01; Vol. 60 (10), pp. 5268-5272. Date of Electronic Publication: 2021 Jan 21. - Publication Year :
- 2021
-
Abstract
- The first kinetic resolution of hydroquinoline derivatives with α,α-disubstitution has been achieved through asymmetric remote aminations with azodicarboxylates enabled by chiral phosphoric acid catalysis. Mechanistic studies suggest a monomeric catalyst pathway proceeding through rate- and enantio-determining electrophilic attack promoted by a network of attractive non-covalent interactions between the substrate and catalyst. Facile subsequent removal and transformations of the newly introduced hydrazine moiety enable these protocols to serve as powerful tools for asymmetric synthesis of N-heterocycles with α,α-disubstitution.<br /> (© 2020 Wiley‐VCH GmbH.)
Details
- Language :
- English
- ISSN :
- 1521-3773
- Volume :
- 60
- Issue :
- 10
- Database :
- MEDLINE
- Journal :
- Angewandte Chemie (International ed. in English)
- Publication Type :
- Academic Journal
- Accession number :
- 33620130
- Full Text :
- https://doi.org/10.1002/anie.202015008