Journal
ORGANIC LETTERS
Volume 24, Issue 22, Pages 4052-4057Publisher
AMER CHEMICAL SOC
DOI: 10.1021/acs.orglett.2c01510
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Funding
- National Natural Science Foundation of China [22171029, 21901024, 21871252, 21801024, 21801026]
- Sichuan Science and Technology Program [2021YFS0315]
- Chengdu University [2081919035, 2081921038]
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In this study, the enantioselective desymmetrization of N-arylmaleimides was achieved using a Cu(OTf)(2)/chiral ferrocenyl P,N-ligand complex as a catalyst, through the asymmetric 1,3-dipolar cycloaddition reaction of N-2,2,2-trifluoroethylisatin ketimines. A series of structurally diverse F3C-containing octahydropyrrolo[3,4-c]pyrroles, bearing four contiguous carbon stereocenters and one stereogenic chiral C-N axial bond, were obtained with excellent results (<= 99% yield, >20:1 dr, and 99% ee).
With a Cu(OTf)(2)/chiral ferrocenyl P,N-ligand complex as a catalyst, the enantioselective desymmetrization of N-arylmaleimides was successfully realized by taking advantage of the asymmetric 1,3-dipolar cycloaddition reaction of N-2,2,2-trifluoroethylisatin ketimines. A series of structurally diverse F3C-containing octahydropyrrolo[3,4-c]pyrroles, bearing four contiguous carbon stereocenters and one stereogenic chiral C-N axial bond, were obtained with excellent results (<= 99% yield, >20:1 dr, and 99% ee).
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