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  

作　　者：LIU Guo-Hua YU Han XUE Yun-Ning YAO Mei FANG Hai-Bin 

机构地区：[1]Department of Chemistry, College of Life and Environmental Science, Shanghai Normal University, Shanghai 200234, China

出　　处：《Chinese Journal of Structural Chemistry》2007年第2期133-138,共6页结构化学（英文）

基　　金：Supported by the Shanghai Municipal Education Commission (No. 05D215);Shanghai Science and Technology Development Fund (No. 05JC14074);National Natural Science Foundation of China (No. 20543007 and 20673072)

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/HCl 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/cm^3, F（000） = 556, R = 0.0745, wR = 0.1933 and #（MoKa） = 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.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/HCl 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/cm^3, F（000） = 556, R = 0.0745, wR = 0.1933 and #（MoKa） = 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.

关 键 词：crystal structure BINOL derivative asymmetric addition 

分 类 号：O625.151[理学—有机化学]