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Volumn 10, Issue 21, 2008, Pages 4759-4762

Trans-stereoselectivity in the reaction between homophthalic anhydride and imines

Author keywords

[No Author keywords available]

Indexed keywords

IMINE; PHTHALIC ANHYDRIDE;

EID: 58149156306     PISSN: 15237060     EISSN: None     Source Type: Journal    
DOI: 10.1021/ol801757r     Document Type: Article
Times cited : (40)

References (30)
  • 17
    • 60949099050 scopus 로고    scopus 로고
    • 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
    • 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.
  • 18
    • 0000842304 scopus 로고
    • Density-functional theory (DFT) calculations were carried out using the B3LYP hybrid functional. See: (a) Becke, A. D
    • Density-functional theory (DFT) calculations were carried out using the B3LYP hybrid functional. See: (a) Becke, A. D. J. Chem. Phys. 1993, 98, 5648.
    • (1993) J. Chem. Phys , vol.98 , pp. 5648
  • 20
    • 0000216001 scopus 로고
    • 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
    • (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:
    • (1980) Can. J. Phys , vol.58 , pp. 1200
    • Vosko, S.H.1    Wilk, L.2    Nusair, M.3
  • 22
    • 60949112600 scopus 로고    scopus 로고
    • 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).
    • 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).


* 이 정보는 Elsevier사의 SCOPUS DB에서 KISTI가 분석하여 추출한 것입니다.