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Volumn , Issue 3, 2000, Pages 397-399

Synthetic study on oximidines: A concise synthesis of (Z)-enamides

Author keywords

Curtius rearrangement; DPPA; Enamide; Isocyanate; Oximidine

Indexed keywords

ENAMINE; ISOCYANATE; OXIME;

EID: 0034048696     PISSN: 09365214     EISSN: None     Source Type: Journal    
DOI: None     Document Type: Article
Times cited : (72)

References (20)
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    • Ben-Ishai, D.; Gigee, R. Tetrahedron Lett. 1965, 4523. Smith, M. B.; Wang, C. -J.; Keusenkothen, P. F.; Dembofsky, B. T.; Fay, J. G.; Zezza, C. A.; Kwon, T. W.; Sheu, J.; Son, Y. C.; Menezens, R. F. Chem. Lett. 1992, 247.
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    • Ziegenbein, W.1    Franke, W.2
  • 10
    • 0003066765 scopus 로고
    • Brettle, R. and Mosedal, A. J. has reported a regioselective synthesis of enamides, based on the Curtius rearrangement and acylation of enecarbamate: Brettle, R.; Mosedal. A, J. J. Chem. Soc. Perkin Trans. I 1988, 2185.
    • (1988) J. Chem. Soc. Perkin Trans. , vol.1 , pp. 2185
    • Brettle, R.1    Mosedal, A.J.2
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    • Weinstock, J. J. Org. Chem. 1961, 26, 3511. Kraiser, C.; Weinstock, J. Org. Synth. 1971, 51, 48.
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    • note
    • 2-3) was 11.7 Hz.
  • 15
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    • note
    • 3. (Equation presented)
  • 16
    • 0015520853 scopus 로고
    • Shioiri, T.; Ninomiya, K.; Yamada, S. J. Am. Chem. Soc. 1972, 94, 6203. Ninomiya, K.; Shioiri, T.; Yamada, S. Tetrahedron 1974, 30, 2151. Taber, D. F.; Yu, H.; Incarvito, D.; Rheingold, A. L. J. Am. Chem. Soc. 1998, 120, 13285.
    • (1972) J. Am. Chem. Soc. , vol.94 , pp. 6203
    • Shioiri, T.1    Ninomiya, K.2    Yamada, S.3
  • 17
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    • Shioiri, T.; Ninomiya, K.; Yamada, S. J. Am. Chem. Soc. 1972, 94, 6203. Ninomiya, K.; Shioiri, T.; Yamada, S. Tetrahedron 1974, 30, 2151. Taber, D. F.; Yu, H.; Incarvito, D.; Rheingold, A. L. J. Am. Chem. Soc. 1998, 120, 13285.
    • (1974) Tetrahedron , vol.30 , pp. 2151
    • Ninomiya, K.1    Shioiri, T.2    Yamada, S.3
  • 18
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    • Shioiri, T.; Ninomiya, K.; Yamada, S. J. Am. Chem. Soc. 1972, 94, 6203. Ninomiya, K.; Shioiri, T.; Yamada, S. Tetrahedron 1974, 30, 2151. Taber, D. F.; Yu, H.; Incarvito, D.; Rheingold, A. L. J. Am. Chem. Soc. 1998, 120, 13285.
    • (1998) J. Am. Chem. Soc. , vol.120 , pp. 13285
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  • 19
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    • note
    • 2K (3.1eq.), AcOH (5.2eq.) / MeOH-pyridine, 61%.
  • 20
    • 0343258526 scopus 로고    scopus 로고
    • note
    • The compound 10 was unstable even at -78°C. Prolonged reaction time caused the decomposition of 10. We found that 10 was relatively stable in hexane or ether.


* 이 정보는 Elsevier사의 SCOPUS DB에서 KISTI가 분석하여 추출한 것입니다.