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Rhodium-Catalyzed Ortho-Olefination of Sterically Demanding Benzamides: Application to Asymmetric Synthesis of Axially Chiral Benzamides.

It has been established that an unsubstituted cyclopentadienyl rhodium(III) (CpRh III ) 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 CpRh III -catalyzed diastereoselective ortho C-H bond olefination enabled the asymmetric synthesis of axially chiral N , N- dialkylbenzamide derivatives with high ee values.