| A New Convenient Method for the Resolution of 1, 1'-Binaphthalene-2, 2'-diol Via a Phosphite Using (-)-Menthol as Resolving Agent |
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| 作者姓名： | Jue Xiao CAI Zheng Hong ZHOU Kang Ying LI Chi Hung YEUNG Chu Chi TANG* State Key Laboratory of Elemento-Organic Chemistry Institute of Elemento-Organic Chemistry Nankai University Tianjin Open Laboratory of Chirotechnology and D |
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| 作者单位： | Jue Xiao CAI1，Zheng Hong ZHOU1，Kang Ying LI1，Chi Hung YEUNG2，Chu Chi TANG1* 1State Key Laboratory of Elemento-Organic Chemistry，Institute of Elemento-Organic Chemistry，Nankai University，Tianjin，300071 2Open Laboratory of Chirotechnology and D |
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| 基金项目： | Financial Support by the National Natural Science Foundation of China (No.29872016)，the Hong Kong Polytechnic University ASD Fund are gratefully acknowledged. |
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| 摘 要： | Optically active 1,1-binaphthalene-2, 2-diol has become a quite important chiral source in different fields of chirotechnology, especially in asymmetric synthesis1. Its synthesis and resolution has been extensively studied and various resolution methods have been reported2. Among the reported resolution methods, the following three, namely, via the formation of phosphoric acid derivatives3, boric acid derivatives4 and inclusion complexes5, are the most important. OHOH+_( )-1(-)-(S)-1(+)-(R)…
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A New Convenient Method for the Resolution of 1, 1'-Binaphthalene-2, 2'-diol Via a Phosphite Using (-)-Menthol as Resolving Agent |
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| Jue Xiao CAI,Zheng Hong ZHOU,Kang Ying LI,Chi Hung YEUNG,Chu Chi TANG* State Key Laboratory of Elemento-Organic Chemistry,Institute of Elemento-Organic Chemistry,Nankai University,Tianjin, Open Laboratory of Chirotechnology and D.A New Convenient Method for the Resolution of 1, 1''''-Binaphthalene-2, 2''''-diol Via a Phosphite Using (-)-Menthol as Resolving Agent[J].Chinese Chemical Letters,2002,13(7). |
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| Authors: | Jue Xiao CAI Zheng Hong ZHOU Kang Ying LI Chi Hung YEUNG Chu Chi TANG |
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| Abstract: | Menthol reacts with phosphorus trichloride to afford menthyl phosphorodichloridite 2, which further reacts with racemic 1, 1-binaphthalene-2, 2-diol to give phosphite (+)-3 in the presence of triethylamine. (+)-3 can be easily separated by fractional crystallization to form the crystal (+)-(S)-3 and the mother liquor (-)-(R)-3. Then both the crystal and the mother liquor are treated with AcOH-H2O to obtain enantiomeric pure (-)-(S)-1 and (+)-(R)-1 respectively, with enantiomeric excess up to 99.7%. |
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| Keywords: | optically active 1 1-binaphthalene-2 2-diol L-menthol phosphite fractional crystal- lization resolution |
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