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Catalytic Asymmetric Imine Cross-Coupling Reaction.
- Source :
-
Journal of the American Chemical Society [J Am Chem Soc] 2023 Mar 01; Vol. 145 (8), pp. 4400-4407. Date of Electronic Publication: 2023 Feb 17. - Publication Year :
- 2023
-
Abstract
- Catalytic asymmetric cross-coupling of imines constitutes a particularly desirable method for the synthesis of chiral vicinal diamines directly from readily available achiral precursors. The potential of this method lies in the possibility of utilizing a variety of imines as reacting partners. However, the realization of highly stereoselective cross-coupling of two different imines proved to be a formidable challenge. Herein we report an unprecedented catalytic asymmetric cross-coupling reaction that tolerates a variety of ketimines and aldimines as nucleophiles and electrophiles, respectively. The realization of this reaction resulted from the development of a new chiral ammonium catalyst, which was guided by insights from studies of catalyst-substrate interactions. With a 0.5 mol % loading of an organocatalyst, this reaction proceeded in a highly diastereo- and enantioselective manner to afford a diverse range of chiral vicinal diamines as nearly single stereoisomers. This catalytic reaction establishes a new approach for the asymmetric synthesis of chiral vicinal diamines.
Details
- Language :
- English
- ISSN :
- 1520-5126
- Volume :
- 145
- Issue :
- 8
- Database :
- MEDLINE
- Journal :
- Journal of the American Chemical Society
- Publication Type :
- Academic Journal
- Accession number :
- 36800284
- Full Text :
- https://doi.org/10.1021/jacs.3c00051