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Volumn 7, Issue 4, 2005, Pages 637-640

Palladium-catalyzed allylation of imines with allyl alcohols

Author keywords

[No Author keywords available]

Indexed keywords

ALDEHYDE; ALLYL ALCOHOL; ALLYLAMINE DERIVATIVE; IMINE; PALLADIUM;

EID: 14844346557     PISSN: 15237060     EISSN: None     Source Type: Journal    
DOI: 10.1021/ol047609f     Document Type: Article
Times cited : (56)

References (34)
  • 1
    • 0036666324 scopus 로고    scopus 로고
    • For recent reviews on allylation of aldehydes and imines, see: (a) Puentes, C. O.; Kouznetsov, V. J. Heterocycl. Chem. 2002, 39, 595. (b) Denmark, S. E.; Almstead, N. G. In Modern Carbonyl Chemistry; Otera, J., Ed.; Wiley-VHC: Weinheim, 2000; Chapter 10. (c) Chemler, S. R.; Roush, R. W. In Modern Carbonyl Chemistry; Otera, J., Ed.; Wiley-VHC: Weinheim, 2000; Chapter 11. (d) Kobayashi, S.; Ishitani, H. Chem. Rev. 1999, 99, 1069.
    • (2002) Heterocycl. Chem. , vol.39 , pp. 595
    • Puentes, C.O.1    Kouznetsov, V.J.2
  • 2
    • 0036666324 scopus 로고    scopus 로고
    • Otera, J., Ed.; Wiley-VHC: Weinheim, Chapter 10
    • For recent reviews on allylation of aldehydes and imines, see: (a) Puentes, C. O.; Kouznetsov, V. J. Heterocycl. Chem. 2002, 39, 595. (b) Denmark, S. E.; Almstead, N. G. In Modern Carbonyl Chemistry; Otera, J., Ed.; Wiley-VHC: Weinheim, 2000; Chapter 10. (c) Chemler, S. R.; Roush, R. W. In Modern Carbonyl Chemistry; Otera, J., Ed.; Wiley-VHC: Weinheim, 2000; Chapter 11. (d) Kobayashi, S.; Ishitani, H. Chem. Rev. 1999, 99, 1069.
    • (2000) Modern Carbonyl Chemistry
    • Denmark, S.E.1    Almstead, N.G.2
  • 3
    • 0036666324 scopus 로고    scopus 로고
    • Otera, J., Ed.; Wiley-VHC: Weinheim, Chapter 11
    • For recent reviews on allylation of aldehydes and imines, see: (a) Puentes, C. O.; Kouznetsov, V. J. Heterocycl. Chem. 2002, 39, 595. (b) Denmark, S. E.; Almstead, N. G. In Modern Carbonyl Chemistry; Otera, J., Ed.; Wiley-VHC: Weinheim, 2000; Chapter 10. (c) Chemler, S. R.; Roush, R. W. In Modern Carbonyl Chemistry; Otera, J., Ed.; Wiley-VHC: Weinheim, 2000; Chapter 11. (d) Kobayashi, S.; Ishitani, H. Chem. Rev. 1999, 99, 1069.
    • (2000) Modern Carbonyl Chemistry
    • Chemler, S.R.1    Roush, R.W.2
  • 4
    • 0000862669 scopus 로고    scopus 로고
    • For recent reviews on allylation of aldehydes and imines, see: (a) Puentes, C. O.; Kouznetsov, V. J. Heterocycl. Chem. 2002, 39, 595. (b) Denmark, S. E.; Almstead, N. G. In Modern Carbonyl Chemistry; Otera, J., Ed.; Wiley-VHC: Weinheim, 2000; Chapter 10. (c) Chemler, S. R.; Roush, R. W. In Modern Carbonyl Chemistry; Otera, J., Ed.; Wiley-VHC: Weinheim, 2000; Chapter 11. (d) Kobayashi, S.; Ishitani, H. Chem. Rev. 1999, 99, 1069.
    • (1999) Chem. Rev. , vol.99 , pp. 1069
    • Kobayashi, S.1    Ishitani, H.2
  • 9
    • 14844358754 scopus 로고    scopus 로고
    • note
    • Without removing water, reactions become dirty (many tailing spots on TLC) and no allylation products are detected.
  • 11
    • 0001374863 scopus 로고    scopus 로고
    • 2Zn (240 mol %) in THF (3 mL) - n-hexane (1.2 mL) at room temperature, α- and γ-methylallyl alcohols (1 mmol) react with benzaldehyde (1.2 mmol) to provide mixtures of anti- and syn-2-methyl-1-phenyl- 3-buten-1-ols in the same ratio (2.4:1). The same reactions with α- and γ-phenylallyl alcohols provide anti- and syn-1,2-diphenyl-3-buten-1-ols in the same, but in higher ratios of 10:1: Tamaru, Y. J. Organomet. Chem. 1999, 576, 215.
    • (1999) J. Organomet. Chem. , vol.576 , pp. 215
    • Tamaru, Y.1
  • 12
    • 14844359457 scopus 로고    scopus 로고
    • note
    • Under present conditions, 1,3-disubstituted allylic alcohols, such as 1,3-dimethylallyl alcohols and 2-cyclohexenol, failed to give expected homoallylamines.
  • 14
    • 14844346822 scopus 로고    scopus 로고
    • note
    • Crystallographic data (excluding structure factors) for the structure of 2 have been deposited with the Cambridge Crystallographic Data Centre as supplementary publication no. CCDC-256123. Copies of the data can be obtained free of charge on application to CCDC, 12 Union Road. Cambridge CB21EZ. UK (fax: (+44)1223-336-033; e-mail: deposit@ ccdc.cam.ac.uk).
  • 24
    • 14844363474 scopus 로고    scopus 로고
    • note
    • Allylation with allyl alcohol was reported for benzaldehyde-imine using an umpolung technique of π-allylpalladium with indium(I) iodide. Allyl bromide, iodide, acetate, and carbonate showed good yields; however chloride and alcohol moderate and poor yields, respectively. See ref 12b.


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