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Volumn 39, Issue 11, 2000, Pages 1937-1940

Thermal intermolecular hetero Diels - Alder cycloadditions of aldehydes and imines via o-quinone dimethides

Author keywords

Cycloadditions; Heterocycles; Nitrogen heterocycles; Synthetic methods

Indexed keywords

ALDEHYDE DERIVATIVE; IMINE; QUINONE DERIVATIVE;

EID: 0034596073     PISSN: 14337851     EISSN: None     Source Type: Journal    
DOI: 10.1002/1521-3773(20000602)39:11<1937::AID-ANIE1937>3.0.CO;2-E     Document Type: Article
Times cited : (56)

References (34)
  • 2
    • 0000450167 scopus 로고    scopus 로고
    • and references therein
    • J. L. Segura, N. Martin, Chem. Rev. 1999, 99, 3199, and references therein.
    • (1999) Chem. Rev. , vol.99 , pp. 3199
    • Segura, J.L.1    Martin, N.2
  • 16
    • 33845283207 scopus 로고
    • While there are examples of highly activated dienophiles reacting under strictly thermal conditions; a) P. A. Wender, R. M. Keenan, H. Y. Lee, J. Am. Chem. Soc. 1987, 109, 4390;
    • (1987) J. Am. Chem. Soc. , vol.109 , pp. 4390
    • Wender, P.A.1    Keenan, R.M.2    Lee, H.Y.3
  • 17
    • 0009642235 scopus 로고
    • H. simple aliphatic-aldehydes typically require high pressure for noncatalyzed reactions
    • b) A. Hosomi, Y. Sakata, H. Sakurai, H. Tetrahedron Lett. 1985, 26, 5175, simple aliphatic-aldehydes typically require high pressure for noncatalyzed reactions:
    • (1985) Tetrahedron Lett. , vol.26 , pp. 5175
    • Hosomi, A.1    Sakata, Y.2    Sakurai, H.3
  • 27
    • 0342507094 scopus 로고    scopus 로고
    • note
    • In a competition experiment between compounds 4 and 14, 2-cyclohexen-1-one reacted preferentially with 14.
  • 28
    • 0020464967 scopus 로고
    • For information regarding the regiochemistry of 13, see reference [3]
    • The Diels-Alder reaction of 14 with methyl vinyl ketone gave a 4:1 ratio of regioisomers 26:27, while that between 2-eyclohexen-1-one and 14 gave a 2:1 ratio of 28:29. Poor regioselectivity of 4-methoxy-substituted o-quinone dimethides in Diels - Alder cycloadditions is preeedented in reactions with methyl acrylate: Y. Ito, M. Nakatsuka, T. Saegusa, J. Am. Chem. Soc. 1982, 104, 7609. For information regarding the regiochemistry of 13, see reference [3].
    • (1982) J. Am. Chem. Soc. , vol.104 , pp. 7609
    • Ito, Y.1    Nakatsuka, M.2    Saegusa, T.3


* 이 정보는 Elsevier사의 SCOPUS DB에서 KISTI가 분석하여 추출한 것입니다.