4.6 Article

Rhodium-Catalyzed Enantioselective Arylation of Aliphatic Imines

Journal

CHEMISTRY-A EUROPEAN JOURNAL
Volume 22, Issue 23, Pages 7739-7742

Publisher

WILEY-V C H VERLAG GMBH
DOI: 10.1002/chem.201601246

Keywords

asymmetric arylation; cationic rhodium; imines; phosphoramidite; alpha-branched amine

Funding

  1. MEXT (Japan) Strategic Molecular and Materials Chemistry through Innovative Coupling Reactions of Hokkaido University

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Chiral rhodium(I)-catalyzed highly enantioselective arylation of aliphatic N-sulfonyl aldimines with arylboronic acids has been developed. This transformation is achieved by the use of a rhodium/bis(phosphoramidite) catalyst to give enantiomerically enriched a-branched amines (up to 99% ee). In addition, this system enables efficient synthesis of (+)-NPS R-568 and Cinacalcet which are calcimimetic agents.

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