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DOI: 10.1055/s-0034-1378611
Isoindolines via Enantioselective C−H Insertion of Diazo Compounds
Publication History
Publication Date:
18 August 2014 (online)
Significance
Metal-catalyzed direct C−H activation/functionalization has become an attractive method for value-adding aromatic and heteroaromatic derivatization. However, the corresponding asymmetric variants remain far less developed due to the relatively low number of appropriate chiral ligands. The group of Cramer has invented and applied an elegant series of chiral Cp-type ligands for Rh(III)-catalyzed C−H functionalization which afford high levels of selectivities in numerous cases. This is the first report of the use of achiral diazo precursors in this strategy to access enantioenriched N-containing heterocycles.
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Comment
The authors report an asymmetric synthesis of isoindolones via chiral Cp rhodium(III)-catalyzed [Rh] C−H functionalization of aryl hydroxamates with diazo acceptors. Products are obtained in good to excellent yields and high to excellent levels of enantioselectivity under mild reaction conditions. They suggest that the high enantioselectivities observed in this transformation result from the high double steric differentiation of the catalyst–ligand combination and the employed diazo compound in addition to the resulting rhodium carbenoid intermediate.
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