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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• 作者：Yasuike ; Shuji ; Kawara ; Shin-ichiro ; Okajima ; Satoru ; Seki ; Hiroko ; Yamaguchi ; Kentaro ; Kurita ; Jyoji
• 关键词：Antimony and compounds ; Resolution ; Asymmetric reaction ; Palladium and compounds ; Hydrosilylation
• 刊名：Tetrahedron Letters
• 出版年：2004
• 期刊代码：109_00404039
• 类别：ch
• 出版时间：November 29, 2004
• 卷：45
• 期：49
• 页码：9135-9138
• 文件大小：335 K

摘要

A new non-C₂-symmetrical antimony芒芒芒phosphorous ligand, (芒芒)-2-diphenyl-phosphano-2芒芒芒-di(p-tolyl)stibano-1,1芒芒芒-binaphthyl (BINAPSb) 3, has been prepared from 2-bromo-2芒芒芒-diphenylphosphano-1,1芒芒芒-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 (芒芒)-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.