Journal
ANGEWANDTE CHEMIE-INTERNATIONAL EDITION
Volume 60, Issue 22, Pages 12264-12268Publisher
WILEY-V C H VERLAG GMBH
DOI: 10.1002/anie.202016938
Keywords
asymmetric catalysis; axial chirality; desymmetrization; N-heterocyclic carbenes; organocatalysis
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Funding
- SERB, Government of India [DIA/2018/000018]
- KVPY
- IISc
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This study describes the atroposelective synthesis of N-aryl succinimides with axially chiral C-N bonds catalyzed by N-heterocyclic carbenes, achieving good yields and ee values. Preliminary investigations were also conducted on the rotation barrier for the C-N bond, temperature dependence, and detailed DFT studies on the mechanism.
Although the construction of axially chiral C-C bonds leading to the atroposelective synthesis of biaryls and allied compounds are well-known, the related synthesis of compounds bearing axially chiral C-N bonds are relatively rare. Described herein is the N-heterocyclic carbene-catalyzed atroposelective synthesis of N-aryl succinimides having an axially chiral C-N bond via the desymmetrization of N-aryl maleimides. The NHC involved intermolecular Stetter-aldol cascade of dialdehydes with prochiral N-aryl maleimides followed by oxidation afforded N-aryl succinimides in good yields and ee values. Preliminary studies on rotation barrier for the C-N bond, the temperature dependence, and detailed DFT studies on mechanism are also provided.
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