Cu-Catalyzed Asymmetric 1,3-Dipolar Cycloaddition of N -2,2,2-Trifluoroethylisatin Ketimines Enables the Desymmetrization of N -Arylmaleimides: Access to Enantioenriched F 3 C-Containing Octahydropyrrolo[3,4- c ]pyrroles

With a Cu(OTf) /chiral ferrocenyl P,N-ligand complex as a catalyst, the enantioselective desymmetrization of -arylmaleimides was successfully realized by taking advantage of the asymmetric 1,3-dipolar cycloaddition reaction of -2,2,2-trifluoroethylisatin ketimines. A series of structurally diverse F...

Full description

Saved in:
Bibliographic Details
Published in:Organic letters 2022-06, Vol.24 (22), p.4052-4057
Main Authors: Wang, Zhen-Hua, Liu, Ji-Hong, Zhang, Yan-Ping, Zhao, Jian-Qiang, You, Yong, Zhou, Ming-Qiang, Han, Wen-Yong, Yuan, Wei-Cheng
Format: Article
Language:English
Citations: Items that this one cites
Items that cite this one
Online Access:Get full text
Tags: Add Tag
No Tags, Be the first to tag this record!
Description
Summary:With a Cu(OTf) /chiral ferrocenyl P,N-ligand complex as a catalyst, the enantioselective desymmetrization of -arylmaleimides was successfully realized by taking advantage of the asymmetric 1,3-dipolar cycloaddition reaction of -2,2,2-trifluoroethylisatin ketimines. A series of structurally diverse F C-containing octahydropyrrolo[3,4- ]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).
ISSN:1523-7060
1523-7052
DOI:10.1021/acs.orglett.2c01510