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Volumn 55, Issue 49, 1999, Pages 14161-14184

Perilithiation and the synthesis of 8-substituted-1-naphthamides

Author keywords

Amides; Lithiation; Naphthalenes; Polonoski reaction

Indexed keywords

AMIDE; NAPHTHALENE DERIVATIVE;

EID: 0033521051     PISSN: 00404020     EISSN: None     Source Type: Journal    
DOI: 10.1016/S0040-4020(99)00881-9     Document Type: Article
Times cited : (56)

References (57)
  • 28
    • 85038147244 scopus 로고    scopus 로고
    • note
    • 28. For a comment on kinetic vs. thermodynamic selectivity in a similar reaction of naphthyloxazolines, see ref. 34
  • 30
    • 0001665951 scopus 로고
    • 29. Dixon, J. A., Fishman, D. H., Dudinyak, R. S. Tetrahedron Lett. 1964, 613; Dixon, J. A.; Fishman, D. H. J. Am. Chem. Soc. 1963, 85, 1356.
    • (1963) J. Am. Chem. Soc. , vol.85 , pp. 1356
    • Dixon, J.A.1    Fishman, D.H.2
  • 44
    • 0033597159 scopus 로고    scopus 로고
    • 43. The stereochemistry of 18 was assigned as cis by analogy with de-deuterio 12a (E = H), which also has a 0 Hz coupling between H-1 and H-2 [the coupling constant in de-deuterio 12b (E = H) is 13 Hz]. The axial configuration was assigned from the precedent of other naphthamides bearing bulky, chiral 2-substituents: see Clayden, J.; Westlund, N.; Wilson, F. X. Tetrahedron Lett. 1999, 40, 3331.
    • (1999) Tetrahedron Lett. , vol.40 , pp. 3331
    • Clayden, J.1    Westlund, N.2    Wilson, F.X.3
  • 52
    • 0000453193 scopus 로고
    • Evidence that the formyl group is introduced ortho to the amide is provided by the fact that the aldehydes 37-39 are resolvable, chiral compounds: for more details (including crystallographic studies of 15, 16, 17 and 36) see ref. 8 and Clayden J.; McCarthy, C; Helliwell, M. J. Chem. Soc., Chem. Commun, in press.
    • 51. Beak, P.; Kerrick, S. T.; Gallagher, D. J. J. Am. Chem. Soc. 1993, 115, 10628. Evidence that the formyl group is introduced ortho to the amide is provided by the fact that the aldehydes 37-39 are resolvable, chiral compounds: for more details (including crystallographic studies of 15, 16, 17 and 36) see ref. 8 and Clayden J.; McCarthy, C; Helliwell, M. J. Chem. Soc., Chem. Commun, in press.
    • (1993) J. Am. Chem. Soc. , vol.115 , pp. 10628
    • Beak, P.1    Kerrick, S.T.2    Gallagher, D.J.3
  • 57
    • 84872521185 scopus 로고    scopus 로고
    • Bruker AXS Inc., Madison, WI 53719, U.S.A.
    • 56. Sheldrick, G. M., SHELXTL Version 5.10., Bruker AXS Inc., Madison, WI 53719, U.S.A. (1998).
    • (1998) SHELXTL Version 5.10.
    • Sheldrick, G.M.1


* 이 정보는 Elsevier사의 SCOPUS DB에서 KISTI가 분석하여 추출한 것입니다.