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

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) , α = 85.52(2), β = 70.245(13), γ = 76.554(11)o, Z = 2, V = 1352.8(13)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.