| Crystal Structure of （R）-3,3＇- Bis （b enzyloxymethyl）- 1,1 ＇-bi- 2,2＇-naphthol and Its Applications in Enantioselective Lewis Acid Catalyzed Addition of Diethylzinc to Aldehydes |
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| 作者单位： | LIU Guo-Hua（Department of Chemistry, College of Life and Environmental Science, Shanghai Normal University, Shanghai 200234, China） ;
YU Han（Department of Chemistry, College of Life and Environmental Science, Shanghai Normal University, Shanghai 200234, China） ;
XUE Yun-Ning（Department of Chemistry, College of Life and Environmental Science, Shanghai Normal University, Shanghai 200234, China） ;
YAO Mei（Department of Chemistry, College of Life and Environmental Science, Shanghai Normal University, Shanghai 200234, China） ;
FANG Hai-Bin（Department of Chemistry, College of Life and Environmental Science, Shanghai Normal University, Shanghai 200234, China） ; |
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| 基金项目： | 上海市教委资助项目
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上海市科技发展基金
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国家自然科学基金 |
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| 摘 要： | The title compound (R)-3,3'-bis(benzyloxymethyl)-1,1'-bi-2,2'-naphthol (R)-3 has been synthesized through the deprotection of MOM group by iprOH/HC1 in 83% isolated yield and the suitable single crystals for X-ray diffraction were obtained by recrystallization at room temperature from the mixture solvents. Crystallographic data for (R)-3: C36H30O4, Mr = 526.60,triclinic, space group P1, a = 10.057(6), b = 11.934(7), c = 12.314(6) (A), α = 85.52(2), β =70.245(13), γ = 76.554(11)°, Z= 2, V= 1352.8(13) (A)3, Dc = 1.293 g/cm3, F(000) = 556, R = 0.0745,wR = 0.1933 and μ(MoKα) = 0.083 mm-1. The title compound (R)-3 was found to be effective in the enantioselective addition of diethylzinc to aldehydes both in the presence and absence of Ti(OiPr)4. In the latter case, (R)-3 showed much higher catalytic activity and enantioselectivity than (R)-BINOL's.
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| 关 键 词： | 萘酚 晶体结构 衍生物 不对称分析 |
Crystal Structure of (R)-3,3'-Bis(benzyloxymethyl)-1,1 '-bi-2,2'-naphthol and Its Applications in Enantioselective Lewis Acid Catalyzed Addition of Diethylzinc to Aldehydes |
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| Authors: | LIU Guo-Hua YU Han XUE Yun-Ning YAO Mei FANG Hai-Bin |
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| Institution: | Department of Chemistry, College of Life and Environmental Science, Shanghai Normal University, Shanghai 200234, China |
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| Abstract: | The title compound (R)-3,3'-bis(benzyloxymethyl)-1,1'-bi-2,2'-naphthol (R)-3 has been synthesized through the deprotection of MOM group by iprOH/HC1 in 83% isolated yield and the suitable single crystals for X-ray diffraction were obtained by recrystallization at room temperature from the mixture solvents. Crystallographic data for (R)-3: C36H30O4, Mr = 526.60,triclinic, space group P1, a = 10.057(6), b = 11.934(7), c = 12.314(6) (A), α = 85.52(2), β =70.245(13), γ = 76.554(11)°, Z= 2, V= 1352.8(13) (A)3, Dc = 1.293 g/cm3, F(000) = 556, R = 0.0745,wR = 0.1933 and μ(MoKα) = 0.083 mm-1. The title compound (R)-3 was found to be effective in the enantioselective addition of diethylzinc to aldehydes both in the presence and absence of Ti(OiPr)4. In the latter case, (R)-3 showed much higher catalytic activity and enantioselectivity than (R)-BINOL's. |
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| Keywords: | crystal structure BINOL derivative asymmetric addition Structure Crystallographic Aldehydes Diethylzinc Addition Lewis Acid Enantioselective Applications BINOL catalytic activity enantioselectivity case effective enantioselective addition diethylzinc aldehydes presence space data isolated |
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