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Synthesis of 3,3′-Diaryl-Substituted 2,2′-Diamino-1,1′-binaphthyl and Its Derivatives

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posted on 18.06.2010, 00:00 by Masahiro Yoshimura, Toshimitsu Muraoka, Hiroshi Nakatsuka, Hanmin Huang, Masato Kitamura
Substitution at the 3 and/or 3′ position of a binaphthyl skeleton sometimes enhances stereoselectivity during asymmetric reactions. High-yield and stepwise introduction of aryl groups into the 2,2′-diamino derivative has been established for the first time via an ortho-lithiation/iodization/Suzuki−Miyaura coupling protocol. The results described herein will facilitate the synthesis of a variety of 3,3′-substituted 2,2′-diamino-1,1′-binaphthyl compounds, which are key intermediates for obtaining valuable related ligands and organocatalysts.