Barik, Soumen ; Das, Rohan Chandra ; Balanna, Kuruva ; Biju, Akkattu T. (2022) Kinetic Resolution Approach to the Synthesis of C–N Axially Chiral N-Aryl Aminomaleimides via NHC-Catalyzed [3 + 3] Annulation Organic Letters, 24 (29). pp. 5456-5461. ISSN 1523-7060
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Official URL: http://doi.org/10.1021/acs.orglett.2c02185
Related URL: http://dx.doi.org/10.1021/acs.orglett.2c02185
Abstract
Chiral NHC-catalyzed kinetic resolution of N-aryl aminomaleimides allowing the synthesis of C-N axially chiral N-aryl aminomaleimides via remote chirality control is presented. The catalytically generated α,β-unsaturated acylazoliums from 2-bromoenals underwent selective [3 + 3] annulation with one of the enantiomers of maleimide to furnish fused-dihydropyridinone (bearing axial/central chirality, up to 6:1 dr, >99:1 er) leaving the enantioenriched opposite enantiomer (up to >99:1 er). Studies on C-N bond rotation barrier and dependence on temperature are also provided.
| Item Type: | Article |
|---|---|
| Source: | Copyright of this article belongs to American Chemical Society |
| ID Code: | 128575 |
| Deposited On: | 03 Nov 2022 06:38 |
| Last Modified: | 03 Nov 2022 06:38 |
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