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Volumn 119, Issue 42, 1997, Pages 10049-10053

Aldehydes vs aldimines. Unprecedented aldimine-selective nucleophilic additions in the coexistence of aldehydes using a lanthanide salt as a Lewis acid catalyst

Author keywords

[No Author keywords available]

Indexed keywords

ALDEHYDE; IMINE; LANTHANIDE; REAGENT; YTTERBIUM;

EID: 0030669813     PISSN: 00027863     EISSN: None     Source Type: Journal    
DOI: 10.1021/ja971153y     Document Type: Article
Times cited : (163)

References (52)
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    • For example, Yamaguchi, M. In Comprehensive Organic Synthesis; Trost, B. M., Ed.; Pergamon Press: New York, 1991; Vol. 1, Chapter 1.11.
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  • 2
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    • Very recently, Yamamoto et al. reported imine-selective allylation via a palladium catalyzed allylstannane reaction. Nakamura, H.; Iwama, H.; Yamamoto, Y. J. Chem. Soc., Chem. Commun. 1996, 1459; J. Am. Chem. Soc. 1996, 118, 6641.
    • (1996) J. Chem. Soc., Chem. Commun. , pp. 1459
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  • 3
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    • Very recently, Yamamoto et al. reported imine-selective allylation via a palladium catalyzed allylstannane reaction. Nakamura, H.; Iwama, H.; Yamamoto, Y. J. Chem. Soc., Chem. Commun. 1996, 1459; J. Am. Chem. Soc. 1996, 118, 6641.
    • (1996) J. Am. Chem. Soc. , vol.118 , pp. 6641
  • 4
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    • Trost, B. M., Ed.; Pergamon Press: New York, Chapter 2.3
    • (a) Chan, T.-H. In Comprehensive Organic Synthesis; Trost, B. M., Ed.; Pergamon Press: New York, 1991; Vol. 2, Chapter 2.3.
    • (1991) Comprehensive Organic Synthesis , vol.2
    • Chan, T.-H.1
  • 7
    • 0003417469 scopus 로고
    • Trost, B. M., Ed.; Pergamon Press: New York, Chapter 4.1
    • (a) Kleinman, E. F. In Comprehensive Organic Synthesis; Trost, B. M., Ed.; Pergamon Press: New York, 1991: Vol. 2, Chapter 4.1.
    • (1991) Comprehensive Organic Synthesis , vol.2
    • Kleinman, E.F.1
  • 16
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    • Aldehyde
    • We have already found that lanthanide triflates are effective catalysts for the reactions of aldehydes or aldimines with silyl enol ethers or ketene silyl acetals. (a) Aldehyde: Kobayashi, S.; Hachiya, I. Tetrahedron Lett. 1992, 33, 1625. (b) Aldimine: Kobayashi, S.; Araki, M.; Ishitani, H.; Nagayama, S.; Hachiya, I. Synlett 1995, 233. See, also: (c) Kobayashi, S.; Hachiya, I.; Suzuki, S.; Moriwaki, M. Tetrahedron Lett. 1996, 37, 2809.
    • (1992) Tetrahedron Lett. , vol.33 , pp. 1625
    • Kobayashi, S.1    Hachiya, I.2
  • 17
    • 0041753278 scopus 로고
    • Aldimine
    • We have already found that lanthanide triflates are effective catalysts for the reactions of aldehydes or aldimines with silyl enol ethers or ketene silyl acetals. (a) Aldehyde: Kobayashi, S.; Hachiya, I. Tetrahedron Lett. 1992, 33, 1625. (b) Aldimine: Kobayashi, S.; Araki, M.; Ishitani, H.; Nagayama, S.; Hachiya, I. Synlett 1995, 233. See, also: (c) Kobayashi, S.; Hachiya, I.; Suzuki, S.; Moriwaki, M. Tetrahedron Lett. 1996, 37, 2809.
    • (1995) Synlett , pp. 233
    • Kobayashi, S.1    Araki, M.2    Ishitani, H.3    Nagayama, S.4    Hachiya, I.5
  • 18
    • 0029883736 scopus 로고    scopus 로고
    • We have already found that lanthanide triflates are effective catalysts for the reactions of aldehydes or aldimines with silyl enol ethers or ketene silyl acetals. (a) Aldehyde: Kobayashi, S.; Hachiya, I. Tetrahedron Lett. 1992, 33, 1625. (b) Aldimine: Kobayashi, S.; Araki, M.; Ishitani, H.; Nagayama, S.; Hachiya, I. Synlett 1995, 233. See, also: (c) Kobayashi, S.; Hachiya, I.; Suzuki, S.; Moriwaki, M. Tetrahedron Lett. 1996, 37, 2809.
    • (1996) Tetrahedron Lett. , vol.37 , pp. 2809
    • Kobayashi, S.1    Hachiya, I.2    Suzuki, S.3    Moriwaki, M.4
  • 19
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    • 4 was used
    • 4 was used.
  • 20
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    • Morrison, J. D., Ed.; Academic Press: Orlando, FL, Chapter 2
    • Heathcock, C. H. In Asymmetric Synthesis; Morrison, J. D., Ed.; Academic Press: Orlando, FL, 1984; Vol. 3, Chapter 2.
    • (1984) Asymmetric Synthesis , vol.3
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  • 27
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    • (b) Hosomi, A.; Iguchi, H.; Endo, M.; Sakurai, H. Chem. Lett. 1979, 977. Recently, chiral titanium catalysts were shown to be effective in the enantioselective reactions of aldehydes with allyltributylstannane.
    • (1979) Chem. Lett. , pp. 977
    • Hosomi, A.1    Iguchi, H.2    Endo, M.3    Sakurai, H.4
  • 35
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    • It is noted that the yields are much improved compared to those shown in ref 16b
    • It is noted that the yields are much improved compared to those shown in ref 16b.
  • 42
    • 0030788354 scopus 로고    scopus 로고
    • 23 We have several contrary experimental results concerning this proposal, and the present paper is thought to be one of them. Precise discussion will be reported in due course. In addition, these results may open a door to develop chiral Lewis acid catalysis in enantioselective reactions of aldimines with silylated nucleophiles, which is one of the most difficult and challenging themes. Cf.: Ishitani, H.; Ueno, M.; Kobayashi, S. J. Am. Chem. Soc. 1997, 119, 7153.
    • (1997) J. Am. Chem. Soc. , vol.119 , pp. 7153
    • Ishitani, H.1    Ueno, M.2    Kobayashi, S.3


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