메뉴 건너뛰기




Volumn , Issue 13, 2004, Pages 2216-2221

Allyltrimethoxysilane addition to N-acylhydrazones: Two catalytic methods employing CuCl and fluoride

Author keywords

Addition reactions; Allylation; Catalysis; Hydrazones; Silicon

Indexed keywords

ALDEHYDES; AMINES; COPPER COMPOUNDS; HYDRAZINE; KETONES;

EID: 4544315179     PISSN: 00397881     EISSN: None     Source Type: Journal    
DOI: 10.1055/s-2004-829190     Document Type: Article
Times cited : (25)

References (36)
  • 1
    • 0000862669 scopus 로고    scopus 로고
    • Reviews of allyl organometallic addition to C=N bonds: (a) Kobayashi, S.; Ishitani, H. Chem. Rev. 1999, 99, 1069. (b) Bloch, R. Chem. Rev. 1998, 98, 1407. (c) Enders, D.; Reinhold, U. Tetrahedron: Asymmetry 1997, 8, 1895. (d) Denmark, S. E.; Nicaise, O. J.-C. J. Chem. Soc., Chem. Commun. 1996, 999. (e) Yamamoto, Y.; Asao, N. Chem. Rev. 1993, 93, 2207. (f) Kleinman, E. F.; Volkmann, R. A. In Comprehensive Organic Synthesis, Vol. 2; Trost, B. M.; Fleming, I., Eds.; Pergamon: New York, 1991, 975.
    • (1999) Chem. Rev. , vol.99 , pp. 1069
    • Kobayashi, S.1    Ishitani, H.2
  • 2
    • 0038106171 scopus 로고    scopus 로고
    • Reviews of allyl organometallic addition to C=N bonds: (a) Kobayashi, S.; Ishitani, H. Chem. Rev. 1999, 99, 1069. (b) Bloch, R. Chem. Rev. 1998, 98, 1407. (c) Enders, D.; Reinhold, U. Tetrahedron: Asymmetry 1997, 8, 1895. (d) Denmark, S. E.; Nicaise, O. J.-C. J. Chem. Soc., Chem. Commun. 1996, 999. (e) Yamamoto, Y.; Asao, N. Chem. Rev. 1993, 93, 2207. (f) Kleinman, E. F.; Volkmann, R. A. In Comprehensive Organic Synthesis, Vol. 2; Trost, B. M.; Fleming, I., Eds.; Pergamon: New York, 1991, 975.
    • (1998) Chem. Rev. , vol.98 , pp. 1407
    • Bloch, R.1
  • 3
    • 0030924784 scopus 로고    scopus 로고
    • Reviews of allyl organometallic addition to C=N bonds: (a) Kobayashi, S.; Ishitani, H. Chem. Rev. 1999, 99, 1069. (b) Bloch, R. Chem. Rev. 1998, 98, 1407. (c) Enders, D.; Reinhold, U. Tetrahedron: Asymmetry 1997, 8, 1895. (d) Denmark, S. E.; Nicaise, O. J.-C. J. Chem. Soc., Chem. Commun. 1996, 999. (e) Yamamoto, Y.; Asao, N. Chem. Rev. 1993, 93, 2207. (f) Kleinman, E. F.; Volkmann, R. A. In Comprehensive Organic Synthesis, Vol. 2; Trost, B. M.; Fleming, I., Eds.; Pergamon: New York, 1991, 975.
    • (1997) Tetrahedron: Asymmetry , vol.8 , pp. 1895
    • Enders, D.1    Reinhold, U.2
  • 4
    • 0002569664 scopus 로고    scopus 로고
    • Reviews of allyl organometallic addition to C=N bonds: (a) Kobayashi, S.; Ishitani, H. Chem. Rev. 1999, 99, 1069. (b) Bloch, R. Chem. Rev. 1998, 98, 1407. (c) Enders, D.; Reinhold, U. Tetrahedron: Asymmetry 1997, 8, 1895. (d) Denmark, S. E.; Nicaise, O. J.-C. J. Chem. Soc., Chem. Commun. 1996, 999. (e) Yamamoto, Y.; Asao, N. Chem. Rev. 1993, 93, 2207. (f) Kleinman, E. F.; Volkmann, R. A. In Comprehensive Organic Synthesis, Vol. 2; Trost, B. M.; Fleming, I., Eds.; Pergamon: New York, 1991, 975.
    • (1996) J. Chem. Soc., Chem. Commun. , pp. 999
    • Denmark, S.E.1    Nicaise, O.J.-C.2
  • 5
    • 4243893500 scopus 로고
    • Reviews of allyl organometallic addition to C=N bonds: (a) Kobayashi, S.; Ishitani, H. Chem. Rev. 1999, 99, 1069. (b) Bloch, R. Chem. Rev. 1998, 98, 1407. (c) Enders, D.; Reinhold, U. Tetrahedron: Asymmetry 1997, 8, 1895. (d) Denmark, S. E.; Nicaise, O. J.-C. J. Chem. Soc., Chem. Commun. 1996, 999. (e) Yamamoto, Y.; Asao, N. Chem. Rev. 1993, 93, 2207. (f) Kleinman, E. F.; Volkmann, R. A. In Comprehensive Organic Synthesis, Vol. 2; Trost, B. M.; Fleming, I., Eds.; Pergamon: New York, 1991, 975.
    • (1993) Chem. Rev. , vol.93 , pp. 2207
    • Yamamoto, Y.1    Asao, N.2
  • 6
    • 0000018912 scopus 로고
    • Trost, B. M.; Fleming, I., Eds.; Pergamon: New York
    • Reviews of allyl organometallic addition to C=N bonds: (a) Kobayashi, S.; Ishitani, H. Chem. Rev. 1999, 99, 1069. (b) Bloch, R. Chem. Rev. 1998, 98, 1407. (c) Enders, D.; Reinhold, U. Tetrahedron: Asymmetry 1997, 8, 1895. (d) Denmark, S. E.; Nicaise, O. J.-C. J. Chem. Soc., Chem. Commun. 1996, 999. (e) Yamamoto, Y.; Asao, N. Chem. Rev. 1993, 93, 2207. (f) Kleinman, E. F.; Volkmann, R. A. In Comprehensive Organic Synthesis, Vol. 2; Trost, B. M.; Fleming, I., Eds.; Pergamon: New York, 1991, 975.
    • (1991) Comprehensive Organic Synthesis , vol.2 , pp. 975
    • Kleinman, E.F.1    Volkmann, R.A.2
  • 20
    • 4544259645 scopus 로고    scopus 로고
    • note
    • In combination with t-BuOH as proton source, the yield with t-BuBOX improved to 51%, but the enantioselectivity decreased to only 1.8% ee.
  • 21
    • 4544305978 scopus 로고    scopus 로고
    • note
    • 6).
  • 22
    • 4544234031 scopus 로고    scopus 로고
    • note
    • 5b).
  • 23
    • 2542556554 scopus 로고    scopus 로고
    • The availability of the Cu-free achiral pathway may contribute to the low enantioselectivity found in reactions employing chiral ligands. For related observations in Cu(II)-catalyzed Mannich-type additions to iminophosphonates, see: Kobayashi, S.; Kiyohara, H.; Nakamura, Y.; Matsubara, R. J. Am. Chem. Soc. 2004, 126, 6558.
    • (2004) J. Am. Chem. Soc. , vol.126 , pp. 6558
    • Kobayashi, S.1    Kiyohara, H.2    Nakamura, Y.3    Matsubara, R.4
  • 24
    • 0141789851 scopus 로고    scopus 로고
    • Mechanisms of metal-free reactions involving fluoride activation are distinctly different from those in the presence of Cd(II) or Ag(I), where evidence for regeneration of a metal fluoride by Si-F cleavage has been presented: Aoyama, N.; Hamada, T.; Manabe, K.; Kobayashi, S. J. Org. Chem. 2003, 68, 7329.
    • (2003) J. Org. Chem. , vol.68 , pp. 7329
    • Aoyama, N.1    Hamada, T.2    Manabe, K.3    Kobayashi, S.4
  • 25
    • 0001214450 scopus 로고
    • Reviews of nucleophilic activation of allylsilanes: (a) Chuit, C. C.; Corriu, R. J. P.; Reye, C.; Young, J. C. Chem. Rev. 1993, 93, 1371. (b) Kennedy, J. W. J.; Hall, D. G. Angew. Chem. Int. Ed. 2003, 42, 4732.
    • (1993) Chem. Rev. , vol.93 , pp. 1371
    • Chuit, C.C.1    Corriu, R.J.P.2    Reye, C.3    Young, J.C.4
  • 26
    • 0142245730 scopus 로고    scopus 로고
    • Reviews of nucleophilic activation of allylsilanes: (a) Chuit, C. C.; Corriu, R. J. P.; Reye, C.; Young, J. C. Chem. Rev. 1993, 93, 1371. (b) Kennedy, J. W. J.; Hall, D. G. Angew. Chem. Int. Ed. 2003, 42, 4732.
    • (2003) Angew. Chem. Int. Ed. , vol.42 , pp. 4732
    • Kennedy, J.W.J.1    Hall, D.G.2
  • 27
    • 4544301252 scopus 로고    scopus 로고
    • note
    • 10b).


* 이 정보는 Elsevier사의 SCOPUS DB에서 KISTI가 분석하여 추출한 것입니다.