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Photoinduced Cobalt-Catalyzed Desymmetrization of Dialdehydes to Access Axial Chirality.
- Source :
-
Journal of the American Chemical Society [J Am Chem Soc] 2023 Mar 29; Vol. 145 (12), pp. 6944-6952. Date of Electronic Publication: 2023 Mar 15. - Publication Year :
- 2023
-
Abstract
- Enantioselective metallaphotoredox catalysis, which combines photoredox catalysis and asymmetric transition-metal catalysis, has become an effective approach to achieve stereoconvergence under mild conditions. Although many impressive synthetic approaches have been developed to access central chirality, the construction of axial chirality by metallaphotoredox catalysis still remains underexplored. Herein, we report two visible light-induced cobalt-catalyzed asymmetric reductive couplings of biaryl dialdehydes to synthesize axially chiral aldehydes (60 examples, up to 98% yield, >19:1 dr, and >99% ee). This protocol shows good functional group tolerance, broad substrate scope, and excellent diastereo- and enantioselectivity.
Details
- Language :
- English
- ISSN :
- 1520-5126
- Volume :
- 145
- Issue :
- 12
- Database :
- MEDLINE
- Journal :
- Journal of the American Chemical Society
- Publication Type :
- Academic Journal
- Accession number :
- 36920031
- Full Text :
- https://doi.org/10.1021/jacs.3c00462