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Volumn 8, Issue 12, 2006, Pages 2611-2614

Torquoselective 6π-electron electrocyclic ring closure of 1-azatrienes containing acyclic chirality at the C-terminus

Author keywords

[No Author keywords available]

Indexed keywords

HETEROCYCLIC COMPOUND;

EID: 33745546543     PISSN: 15237060     EISSN: None     Source Type: Journal    
DOI: 10.1021/ol060932t     Document Type: Article
Times cited : (62)

References (52)
  • 22
    • 0028920309 scopus 로고
    • For leading references on electrocyclic ring-closures involving 1-azatrienes, see: (a) Maynard, D. F.; Okamura, W. H. J. Org. Chem. 1995, 60, 1763.
    • (1995) J. Org. Chem. , vol.60 , pp. 1763
    • Maynard, D.F.1    Okamura, W.H.2
  • 24
    • 0000052960 scopus 로고
    • For an earlier account, see: (c) Oppolzer, V. W. Angew. Chem. 1972, 22, 1108.
    • (1972) Angew. Chem. , vol.22 , pp. 1108
    • Oppolzer, V.W.1
  • 25
    • 33645919009 scopus 로고    scopus 로고
    • For some recent studies of the ring-closure of azatrienes, see: (a) Meketa, M. L.; Weinreb, S. M. Org. Lett. 2006, 8, 1443.
    • (2006) Org. Lett. , vol.8 , pp. 1443
    • Meketa, M.L.1    Weinreb, S.M.2
  • 27
    • 0037151648 scopus 로고    scopus 로고
    • For recent elegant accounts on stereoselective ring-closure of 1-azatrienes, see: (a) Tanaka, K.; Katsumura, S. J. Am. Chem. Soc. 2002, 124, 9660.
    • (2002) J. Am. Chem. Soc. , vol.124 , pp. 9660
    • Tanaka, K.1    Katsumura, S.2
  • 32
    • 0000938909 scopus 로고
    • Trost, B. M., Fleming, I., Eds.; Paquette, L. A., Vol. Ed.; Pergamon Press: New York
    • For a review on rotational preferences leading to diastereomeric induction during a 6π-electron electrocyclic ring closure, see: Okamura, W. H.; de Lera, A. R. Comprehensive Organic Synthesis; Trost, B. M., Fleming, I., Eds.; Paquette, L. A., Vol. Ed.; Pergamon Press: New York, 1991; Vol. 5, pp 699-750.
    • (1991) Comprehensive Organic Synthesis , vol.5 , pp. 699-750
    • Okamura, W.H.1    De Lera, A.R.2
  • 45
    • 33745558089 scopus 로고    scopus 로고
    • note
    • See the Supporting Information.
  • 47
    • 33745522794 scopus 로고    scopus 로고
    • note
    • Despite our efforts, we were not able to render the reaction of 7 to proceed feasibly with either aminopyrone 21 or amide 22.
  • 48
    • 0000938909 scopus 로고
    • Trost, B. M., Fleming, I., Eds.; Paquette, L. A., Vol. Ed.; Pergamon Press: New York
    • For a review on rotational preferences leading to diastereomeric induction during a 6π-electron electrocyclic ring closure, see: Okamura, W. H.; de Lera, A. R. In Comprehensive Organic Synthesis; Trost, B. M., Fleming, I., Eds.; Paquette, L. A., Vol. Ed.; Pergamon Press: New York, 1991; Vol. 5, pp 699-750.
    • (1991) Comprehensive Organic Synthesis , vol.5 , pp. 699-750
    • Okamura, W.H.1    De Lera, A.R.2
  • 50
    • 33745522095 scopus 로고    scopus 로고
    • note
    • Theoretical calculations using SPARTAN-'02 at B3LYP/6-31G* level were neither conclusive nor consistent as to which diastereomeric isomer is more stable energetically.


* 이 정보는 Elsevier사의 SCOPUS DB에서 KISTI가 분석하여 추출한 것입니다.