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Volumn 71, Issue 23, 2006, Pages 8854-8863

Diastereoselective synthesis of enantiopure morphelines by electrophilic selenium-induced 6-exo cyclizations on chiral 3-allyl-2-hydroxymethylperhydro-1, 3-benzoxazine derivatives

Author keywords

[No Author keywords available]

Indexed keywords

CATALYSIS; HYDROGEN BONDS; SELENIUM COMPOUNDS; STEREOCHEMISTRY; SUBSTITUTION REACTIONS; SYNTHESIS (CHEMICAL); THERMAL EFFECTS;

EID: 33750880412     PISSN: 00223263     EISSN: None     Source Type: Journal    
DOI: 10.1021/jo061547k     Document Type: Article
Times cited : (49)

References (108)
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    • Bartlett, P.A.1
  • 2
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    • J. D., Ed.; Academic Press: New York
    • (b) Bartlett, P. A. In Asymmetric Synthesis; Morrison, J. D., Ed.; Academic Press: New York, 1984; Vol. 3, p 411.
    • (1984) Asymmetric Synthesis; Morrison , vol.3 , pp. 411
    • Bartlett, P.A.1
  • 16
    • 0004112606 scopus 로고
    • Liotta, D., Ed.; Wiley: New York
    • (d) Organoselenium Chemistry; Liotta, D., Ed.; Wiley: New York, 1987.
    • (1987) Organoselenium Chemistry
  • 18
    • 0000229226 scopus 로고
    • Abel, E. W., Stone, F. G. A., Wilkinson, G., Eds.; Pergamon: Oxford
    • (f) Krief, A. In Comprehensive Organometallic Chemistry; Abel, E. W., Stone, F. G. A., Wilkinson, G., Eds.; Pergamon: Oxford, 1995; Vol. 11, p 515.
    • (1995) Comprehensive Organometallic Chemistry , vol.11 , pp. 515
    • Krief, A.1
  • 49
    • 0032904933 scopus 로고    scopus 로고
    • For general reviews on chiral selenium compounds, see
    • For general reviews on chiral selenium compounds, see: (a) Wirth, T. Tetrahedron 1999, 55, 1.
    • (1999) Tetrahedron , vol.55 , pp. 1
    • Wirth, T.1
  • 56
    • 37049083840 scopus 로고
    • Only a few examples of the use of stoichiometric chiral auxiliaries attached on the substrate in cyclofunctionalization reactions promoted by electrophiles have appeared in the literature, and to our knowledge this is the first example on a diastereoselective selenocyclofunctionalization. (a) Fox, D. N. A.; Lathbury, D.; Mahon, M. F.; Molloy, K. C.; Gallagher, T. J. Chem. Soc., Chem. Commun. 1989, 1073.
    • (1989) J. Chem. Soc., Chem. Commun. , pp. 1073
    • Fox, D.N.A.1    Lathbury, D.2    Mahon, M.F.3    Molloy, K.C.4    Gallagher, T.5
  • 100
    • 0025090654 scopus 로고
    • The enhanced reactivity observed in these conditions probably arises from the interaction between the Lewis acid and the chloride anion of the electrophilic reagent. For other examples using PhSeCl in the presence of a Lewis acid, see: (a) Kang, S. H.; Hwang, T. S.; Kim, W. J.; Lim, J. K. Tetrahedron Lett. 1990, 31, 5917.
    • (1990) Tetrahedron Lett. , vol.31 , pp. 5917
    • Kang, S.H.1    Hwang, T.S.2    Kim, W.J.3    Lim, J.K.4
  • 105
    • 33750855343 scopus 로고    scopus 로고
    • note
    • Crystallographic data can be obtained from the Cambridge Crystallographic Data Center, 12 Union Road, Cambridge CB2 1EZ, UK. E-mail: deposit@ccdc.cam.ac. uk.


* 이 정보는 Elsevier사의 SCOPUS DB에서 KISTI가 분석하여 추출한 것입니다.