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Volumn 64, Issue 17, 1999, Pages 6329-6336

Electrophilic and nucleophilic reactivities of the azomethine carbon of SAMP-hydrazones: Stereoselective synthesis of γ-amino ketone derivatives

Author keywords

[No Author keywords available]

Indexed keywords

HYDRAZONE DERIVATIVE; KETONE DERIVATIVE;

EID: 0345240944     PISSN: 00223263     EISSN: None     Source Type: Journal    
DOI: 10.1021/jo990503r     Document Type: Article
Times cited : (40)

References (48)
  • 1
    • 0000179903 scopus 로고
    • Brehme, R. Chem. Ber. 1990, 123, 2039. Brehme, R.; Nikolajewski, H. E. Tetrahedron Lett. 1982, 23, 1131. Brehme, R.; Nikolajewski, H. E. Tetrahedron 1976, 32, 731.
    • (1990) Chem. Ber. , vol.123 , pp. 2039
    • Brehme, R.1
  • 2
    • 0000082761 scopus 로고
    • Brehme, R. Chem. Ber. 1990, 123, 2039. Brehme, R.; Nikolajewski, H. E. Tetrahedron Lett. 1982, 23, 1131. Brehme, R.; Nikolajewski, H. E. Tetrahedron 1976, 32, 731.
    • (1982) Tetrahedron Lett. , vol.23 , pp. 1131
    • Brehme, R.1    Nikolajewski, H.E.2
  • 3
    • 0001167637 scopus 로고
    • Brehme, R. Chem. Ber. 1990, 123, 2039. Brehme, R.; Nikolajewski, H. E. Tetrahedron Lett. 1982, 23, 1131. Brehme, R.; Nikolajewski, H. E. Tetrahedron 1976, 32, 731.
    • (1976) Tetrahedron , vol.32 , pp. 731
    • Brehme, R.1    Nikolajewski, H.E.2
  • 14
    • 0000716787 scopus 로고
    • Trost, B. M., Fleming, I., Eds.; Pergamon: Oxford, U.K., Chapter 1.12
    • Volkmann A. V. In Comprehensive Organic Synthesis; Trost, B. M., Fleming, I., Eds.; Pergamon: Oxford, U.K., 1991; Vol. 1, Chapter 1.12.
    • (1991) Comprehensive Organic Synthesis , vol.1
    • Volkmann, A.V.1
  • 18
    • 0030924784 scopus 로고    scopus 로고
    • For a recent, comprehensive review on asymmetric addition of organometallics to the CN double bond of hydrazones see: Enders, D.; Reinhold, U. Tetrahedron Asymmetry 1997, 8, 1895.
    • (1997) Tetrahedron Asymmetry , vol.8 , pp. 1895
    • Enders, D.1    Reinhold, U.2
  • 19
    • 0001448995 scopus 로고    scopus 로고
    • ( 11) Very recently, Kobayashi et al. have reported on the rare earth triflate-catalyzed addition of silyl enolates to monoacylhydrazones: (a) Oyamada, H.; Kobayashi, S. Synlett 1998, 249.
    • (1998) Synlett , pp. 249
    • Oyamada, H.1    Kobayashi, S.2
  • 20
    • 0000290208 scopus 로고    scopus 로고
    • (b) Kobayashi, S.; Furuta, T.; Sugita, K.; Oyamada, H. Synlett 1998, 1019. The addition of these weaker nucleophiles, however, appears to be restricted to activated hydrazones.
    • (1998) Synlett , vol.1019
    • Kobayashi, S.1    Furuta, T.2    Sugita, K.3    Oyamada, H.4
  • 31
    • 0000889671 scopus 로고
    • (a) Imamoto, T.; Sugiura, Y.; Takiyama, N.; Tetrahedron Lett. 1984, 25, 4233.
    • (1984) Tetrahedron Lett. , vol.25 , pp. 4233
  • 36
    • 0345034044 scopus 로고    scopus 로고
    • note
    • It should be noted that the steric differences between the "small" (methyl) and "medium" (methylene in the ring) substituents in these cases are clearly less than for the tertiary compound.
  • 37
    • 0000642086 scopus 로고
    • and references therein
    • Organocerium compounds are claimed to possess better nucleophilicity and less basic character than organolithium or Grignard reagents: Denmark, S. E.; Edwards, J. P.; Nicaise, O. J. Org. Chem. 1993, 58, 8, 569 and references therein.
    • (1993) J. Org. Chem. , vol.58 , Issue.8 , pp. 569
    • Denmark, S.E.1    Edwards, J.P.2    Nicaise, O.3
  • 39
    • 0344603117 scopus 로고    scopus 로고
    • note
    • It is important to wash the catalyst repeatedly with water to neutrality and then with methanol prior to use. Direct washing of the catalyst with methanol resulted in the unexpected N-methylation of the resulting amines. For instance, up to 39% of the N,N-dimethylamine derivative shown in Figure 1 was obtained from 5b under these conditions.
  • 43
    • 49649133169 scopus 로고
    • (a) Hehre, W. J.; Ditchfield, R.; Pople, J. A. J. Chem. Phys. 1972, 56, 2257. Hariharan, P. C.; Pople, J. A. Chem. Phys. Lett. 1972, 66, 217.
    • (1972) Chem. Phys. Lett. , vol.66 , pp. 217
    • Hariharan, P.C.1    Pople, J.A.2
  • 47
    • 0345034039 scopus 로고    scopus 로고
    • Unpublished results
    • In full analogy with enamines, the nucleophilic character of the azomethine carbon of hydrazones demands an effective conjugation between the amino nitrogen and the CN double bond. Consequently, the electrophilic, imine-like reactivity of hydrazones requires the loss of conjugation and, hence, conformations clearly deviated from planarity. Pappalardo, R. R.; Muñoz, J. M.; Fernández, R.; Lassaletta, J. M., Unpublished results.
    • Pappalardo, R.R.1    Muñoz, J.M.2    Fernández, R.3    Lassaletta, J.M.4


* 이 정보는 Elsevier사의 SCOPUS DB에서 KISTI가 분석하여 추출한 것입니다.