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Typical experimental procedure: To a stirred solution of homophthalic anhydride 1 (1 mmol, 0.162 g) in 2 mL of dichloromethane was added 1 M TiCl 4 in dichloromethane (1 mL) at 0 °C under argon atmosphere. After 5 min at 0 °C, DIPEA (1 mmol, 0.17 mL) was added at the same temperature. After stirring for 20 min, a solution of 1 mmol of the corresponding imine 2 in 2 mL of dichloromethane was added dropwise. The reaction mixture was stirred at room temperature for 3 h. The resulting mixture was washed three times with saturated solution of NH4Cl (3 × 5 mL, dried with Na2SO4, evaporated, and purified by flash chromatography (Silicagel 60 230-400 mesh, ethyl acetate/hexane 1:1 and then 5:1) to yield the corresponding product trans-3
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4, evaporated, and purified by flash chromatography (Silicagel 60 230-400 mesh, ethyl acetate/hexane 1:1 and then 5:1) to yield the corresponding product trans-3.
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0000842304
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Density-functional theory (DFT) calculations were carried out using the B3LYP hybrid functional. See: (a) Becke, A. D
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The 6-31G* basis set was used for all atoms except for titanium, which was computed using the LANL2DZ effective core potential and basis set. See
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(c) Vosko, S. H.; Wilk, L.; Nusair, M. Can. J. Phys. 1980, 58, 1200. The 6-31G* basis set was used for all atoms except for titanium, which was computed using the LANL2DZ effective core potential and basis set. See:
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60949112600
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All the calculations reported in this work were carried out using the GaussianOS (Rev. D.02) suite of programs: Frisch, M. J. Gaussian03, revision D.02; Gaussian, Inc.: Wallingford, CT, 2004 (full reference is given in the Supporting Information).
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All the calculations reported in this work were carried out using the GaussianOS (Rev. D.02) suite of programs: Frisch, M. J. Gaussian03, revision D.02; Gaussian, Inc.: Wallingford, CT, 2004 (full reference is given in the Supporting Information).
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