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Organic Letters
Volumn 11, Issue 12, 2009, Pages 2647-2649
Titanium(IV) halide mediated coupling of alkoxides and alkynes: An efficient and stereoselective route to trisubstituted (E)-alkenyl halides
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EID: 67149115140     PISSN: 15237060     EISSN: None     Source Type: Journal    
DOI: 10.1021/ol900669t     Document Type: Article
Times cited : (21)
References (27)
  • 3
    • 37649007817 scopus 로고    scopus 로고
    • Recent reports related to transition-metal-free nucleophilic substitution of hydroxyl groups with alkenyl moieties. See: (a) Morgan, I. R, Yazici, A, Pyne, S. G. Tetrahedron 2008, 64, 1409
    • Recent reports related to transition-metal-free nucleophilic substitution of hydroxyl groups with alkenyl moieties. See: (a) Morgan, I. R.; Yazici, A.; Pyne, S. G. Tetrahedron 2008, 64, 1409
  • 18
    • 58849111259 scopus 로고    scopus 로고
    • 2 was reported. The low stereoselectivity, we believe, is due to the enhanced reaction temperature. Liu, Z.-Q.; Wang, J.; Han, J.; Zhou, B. Tetrahedron Lett. 2009, 50, 1240.
    • 2 was reported. The low stereoselectivity, we believe, is due to the enhanced reaction temperature. Liu, Z.-Q.; Wang, J.; Han, J.; Zhou, B. Tetrahedron Lett. 2009, 50, 1240.
  • 20
    • 84868995578 scopus 로고    scopus 로고
    • Typical reaction procedure: Diphenylmethanol (276 mg, 1.5 mmol) and dichloromethane (15 mL) were placed in a dry, argon-flushed, 100 mL round-bottomed flask equipped with a magnetic stirring bar. The solution was cooled to 0 °C in an ice bath and n-butyllithium (1.6 mmol, 1.6 mL of a 1.0 M hexanes solution) was added via syringe. The solution was allowed to stir for 10 minutes at 0 °C and then for 30 minutes at room temperature. Phenylacetylene (0.16 mL, 1.5 mmol) was added via syringe, followed by titanium(IV) chloride (1.65 mmol, 1.65 mL of a 1.0 M dichloromethane solution, The reaction solution gradually turned dark purple and was allowed to react overnight. The resulting mixture was hydrolyzed with water (15 mL) and extracted into dichloromethane (3 × 15 mL, The organic layer was separated and dried over anhydrous MgSO4. Product la (356 mg, ElZ, 96:4, 78% yield) was isolated by flash column chromatography, using hexanes as eluent
    • 4. Product la (356 mg, ElZ = 96:4, 78% yield) was isolated by flash column chromatography, using hexanes as eluent.
  • 21
    • 67149108741 scopus 로고    scopus 로고
    • For details of the crystallographic data of compound Id, see Supporting Information
    • For details of the crystallographic data of compound Id, see Supporting Information.
  • 22
    • 67149112256 scopus 로고    scopus 로고
    • The stereoselectivity can be readily determined using 1H NMR since the resonances for vinyl protons and allylic protons in the E-isomer and Z-isomer are quite different. Generally, the allylic proton in the E-isomer appears near 4.80 ppm, whch is upfield compared to the corresponding proton in the Z-isomer (generally found near 5.40 ppm).
    • The stereoselectivity can be readily determined using 1H NMR since the resonances for vinyl protons and allylic protons in the E-isomer and Z-isomer are quite different. Generally, the allylic proton in the E-isomer appears near 4.80 ppm, whch is upfield compared to the corresponding proton in the Z-isomer (generally found near 5.40 ppm).
  • 23
    • 84868988704 scopus 로고    scopus 로고
    • n-1], see: (a) Kabalka, G. W.; Yao, M.-L.; Borella, S.; Quick, T. J. Chem. Soc: Dalton Trans. 2008, 776
    • n-1], see: (a) Kabalka, G. W.; Yao, M.-L.; Borella, S.; Quick, T. J. Chem. Soc: Dalton Trans. 2008, 776

* 이 정보는 Elsevier사의 SCOPUS DB에서 KISTI가 분석하여 추출한 것입니다.