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Volumn , Issue 9, 2000, Pages 1363-1378

Atroposelective attack of nucleophiles on 2-formyl-1-naphthamides and their derivatives: Chelation and non-chelation control

Author keywords

[No Author keywords available]

Indexed keywords

ALCOHOLS; AMINES; CHELATION; ETHERS;

EID: 0034616479     PISSN: 14704358     EISSN: None     Source Type: Journal    
DOI: 10.1039/b000669f     Document Type: Article
Times cited : (41)

References (67)
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    • Huryn, D.M.1
  • 16
    • 0011173972 scopus 로고
    • ed. J. D. Morrison, Academic Press, New York
    • E. L. Eliel, in Asymmetric Synthesis, ed. J. D. Morrison, Academic Press, New York, 1983, vol. 2, p. 132.
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    • Eliel, E.L.1
  • 29
    • 0033527779 scopus 로고    scopus 로고
    • For further examples of organolithium additions to naphthalene rings, see references 2 and 28. See also J. Clayden, N. Westlund and F. X. Wilson, Tetrahedron Lett., 1999, 40, 7883;
    • (1999) Tetrahedron Lett. , vol.40 , pp. 7883
    • Clayden, J.1    Westlund, N.2    Wilson, F.X.3
  • 48
    • 0011249155 scopus 로고    scopus 로고
    • For an example of an alkynylaluminium ate complex as a nucleophile, see J. H. Ahn, T. B. Kim, M. J. Joung and N. M. Yoon, Bull. Korean Chem. Soc., 1996, 17, 380. For the use of alkynyl-aluminiums as nucleophiles, see reference 22.
    • (1996) Bull. Korean Chem. Soc. , vol.17 , pp. 380
    • Ahn, J.H.1    Kim, T.B.2    Joung, M.J.3    Yoon, N.M.4
  • 49
    • 33845470050 scopus 로고
    • For an example of a DIBAL-BuLi ate complex as a reducing agent, see S. Kim and K. H. Ahn, J. Org. Chem, 1984, 49, 1717.
    • (1984) J. Org. Chem , vol.49 , pp. 1717
    • Kim, S.1    Ahn, K.H.2
  • 57
    • 0000585729 scopus 로고
    • Similar reasoning has been used to explain the favoured geometry of some amide enolates: see A. G. Schultz and N. J. Green, J. Am. Chem. Soc., 1991, 113, 4931.
    • (1991) J. Am. Chem. Soc. , vol.113 , pp. 4931
    • Schultz, A.G.1    Green, N.J.2
  • 58
    • 33845551861 scopus 로고
    • For simplicity we assume that the oxonium ions are intermediates in the reaction of the acetals under Lewis-acid catalysis. There is evidence that this need not be the case. See P. A. Bartlett, W. S. Johnson and J. D. Elliott, J. Am. Chem. Soc., 1983, 105, 2088;
    • (1983) J. Am. Chem. Soc. , vol.105 , pp. 2088
    • Bartlett, P.A.1    Johnson, W.S.2    Elliott, J.D.3
  • 62
    • 0011167858 scopus 로고
    • ed. B. M. Trost and I. Fleming, Pergamon, Oxford
    • I. Fleming, in Comprehensive Organic Synthesis, ed. B. M. Trost and I. Fleming, Pergamon, Oxford, 1990, vol. 2, p. 576.
    • (1990) Comprehensive Organic Synthesis , vol.2 , pp. 576
    • Fleming, I.1
  • 67
    • 0004150157 scopus 로고    scopus 로고
    • Bruker AXS Inc., Madison, WI 53719, USA
    • G. M. Sheldrick, SHELXTL, Bruker AXS Inc., Madison, WI 53719, USA, 1997.
    • (1997) SHELXTL
    • Sheldrick, G.M.1


* 이 정보는 Elsevier사의 SCOPUS DB에서 KISTI가 분석하여 추출한 것입니다.