Journal
CHEMISTRY-A EUROPEAN JOURNAL
Volume 26, Issue 22, Pages 4969-4973Publisher
WILEY-V C H VERLAG GMBH
DOI: 10.1002/chem.202000797
Keywords
asymmetric synthesis; axial chiral benzamides; C-H bond functionalization; olefination; rhodium
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Funding
- Japan Society for the Promotion of Science [JP26102004] Funding Source: Medline
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It has been established that an unsubstituted cyclopentadienyl rhodium(III) (CpRhIII) complex is a highly active catalyst for the aerobic oxidative ortho C-H bond olefination of sterically demanding ortho-substituted benzamides with alkenes. This catalysis was successfully applied to the diastereoselective synthesis of axially chiral N,N-dialkylbenzamides. The combination of the ruthenium(II)-catalyzed enantioselective hydrogenation and the CpRhIII-catalyzed diastereoselective ortho C-H bond olefination enabled the asymmetric synthesis of axially chiral N,N-dialkylbenzamide derivatives with high ee values.
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