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Non-C2-symmetrical antimony-phosphorus ligand, (R/S)-2-diphenylphosphano-2′-di(p-tolyl)stibano-1,1′-binaphthyl (BINAPSb): preparation and its use for asymmetric reactions as a chiral auxiliary |
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| Authors: | Shuji Yasuike Satoru Okajima Kentaro Yamaguchi |
| Institution: | a Faculty of Pharmaceutical Sciences, Hokuriku University, Kanagawa-machi, Kanazawa 920-1181, Japan b Chemical Analysis Center, Chiba University, 1-33 Yayoicho, Inage-ku, Chiba 263-8522, Japan c Faculty of Pharmaceutical Sciences at Kagawa Campus, Tokushima Bunri University, Shido, Sanuki-city, Kagawa 769-2193, Japan |
| Abstract: | A new non-C2-symmetrical antimony-phosphorous ligand, (±)-2-diphenyl-phosphano-2′-di(p-tolyl)stibano-1,1′-binaphthyl (BINAPSb) 3, has been prepared from 2-bromo-2′-diphenylphosphano-1,1′-naphthyl 4 via its borane complex 6, and could be resolved by the separation of a mixture of the diastereomeric palladium complexes 8A and 8B derived from the reaction of (±)-3 with optically active palladium reagent (S)-7. The enantiomerically pure BINAPSb 3 has proved to be highly effective in the palladium-catalyzed asymmetric hydrosilylation of styrene as a chiral auxiliary. |
| Keywords: | Antimony and compounds Resolution Asymmetric reaction Palladium and compounds Hydrosilylation |
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