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Volumn 5, Issue 4, 2008, Pages 286-289

The Henry reaction efficiently catalyzed by a Cd-proline complex

Author keywords

Aqueous medium; Cd proline complex; Henry reaction; Lewis acid; Mechanism

Indexed keywords


EID: 50249122188     PISSN: 15701786     EISSN: None     Source Type: Journal    
DOI: 10.2174/157017808784049533     Document Type: Article
Times cited : (6)

References (30)
  • 2
    • 0000851805 scopus 로고    scopus 로고
    • Trost, B. M, Ed, Pergamon: Oxford
    • (b) Rosini, G. In Comprehensive Organic Synthesis; Trost, B. M., Ed.; Pergamon: Oxford, 1996; Vol. 2, pp. 321-340;
    • (1996) Comprehensive Organic Synthesis , vol.2 , pp. 321-340
    • Rosini, G.1
  • 7
    • 0032567495 scopus 로고    scopus 로고
    • Adams, H.; Anderson, J. C.; Peace, S.; Pennell, A. M. K J. Org. Chem., 1998, 63, 9932.
    • (b) Adams, H.; Anderson, J. C.; Peace, S.; Pennell, A. M. K J. Org. Chem., 1998, 63, 9932.
  • 26
    • 50249163481 scopus 로고    scopus 로고
    • 5, C, 33.49; H, 5.06; N, 7.81; Found: C, 33.67; H, 4.97; N, 7.86.
    • 5, C, 33.49; H, 5.06; N, 7.81; Found: C, 33.67; H, 4.97; N, 7.86.
  • 28
    • 50249174798 scopus 로고    scopus 로고
    • Representative experimental procedure: the Cd-proline complex (7 mg, 0.02 mmol) was dissolved in 10 mL of H2O and stirred for 3 min. 2,3,4-trimethoxybenzaldehyde (196 mg, 1 mmol) was then added followed by nitromethane (5 mmol, The reaction was stirred at room temperature for 5 h. The organic material was extracted with ethyl acetatc(3 × 10 mL, and the aqueous phase was applied to the next run. The organic phase was washed with brine, dried (Na2SO4, filtered, and the solvent was removed under vacuum. The crude product was purified by passing through a column of silica gel using ethyl acetate: n-hexane(1: 4) as the eluent to provide the desired product 3k as a yellow oil. 1H NMR (300 MHz, CDCl3) δ 7.10 (d, J, 8.7 Hz, 1H, 6.68 (d, J, 8.7 Hz, 1H, 5.55 (t, J, 3.5 Hz 1H, 4.58 (m, 2H, 3.95-3.85 (m, 9H, 3.26 (br, 1H) ppm. 13C NMR (75 MHz, CDCl3) δ 154.6, 150.9, 142.1, 124.0
    • 6 257.09; Found: 257.06.
  • 30
    • 50249188601 scopus 로고    scopus 로고
    • All the compounds were characterized and their structures were confirmed by NMR and elemental analysis. Compound 5d: 1H NNM (300MHz, CDCl3, 7.62-7.37 (m, 10H, 7.35 (m, 4H, 4.88 (m, 3H, 4.29 (m, 1H, 13C NMR (75 MHz, CDCl3, 137.1, 136.3, 135.4, 133.1, 132.9, 132.5, 131.9, 131.2, 130.8, 130.0, 129.0, 128.3, 81.2, 53.4.Anal. Calcd for C20H18ClN2O3P: C, 59,93; H, 4.53; N, 6.99; Found: C, 60.03; H, 4.60; N, 7.64. Compound 5e: 1H NMR (300MHz, CDCl3, 7.57-7.42 (m, 4H, 7.38-7.26 (m, 8H, 7.28 (m, 2H, 4.84 (m, 3H, 4.25 (m, 1H, 13 NMR 75 MHz, CD-Cl3, 137.8, 136.6, 135.4, 133.5, 133.2, 132.9, 132.6, 131.7, 131.2, 131.0, 130.7, 130.1, 129.1, 128.5, 81.6, 52.8. Anal. Calcd for C20H18BrN2O3P: C, 53.95; H, 4.07; N, 6.29; Found: C, 54.13; H, 4.11; N, 6.10
    • 3P: C, 53.95; H, 4.07; N, 6.29; Found: C, 54.13; H, 4.11; N, 6.10.


* 이 정보는 Elsevier사의 SCOPUS DB에서 KISTI가 분석하여 추출한 것입니다.