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Volumn 68, Issue 7, 2003, Pages 2975-2978

Intramolecular Pauson-Khand reactions of α,β-unsaturated esters and related electron-deficient olefins

Author keywords

[No Author keywords available]

Indexed keywords

PAUSON-KHAND REACTIONS;

EID: 0242585428     PISSN: 00223263     EISSN: None     Source Type: Journal    
DOI: 10.1021/jo026828g     Document Type: Article
Times cited : (34)

References (36)
  • 5
    • 33745402207 scopus 로고
    • (e) Schore, N. E. Chem. Rev. 1988, 88, 1081-1119.
    • (1988) Chem. Rev. , vol.88 , pp. 1081-1119
    • Schore, N.E.1
  • 8
    • 0036522941 scopus 로고    scopus 로고
    • For a recent review on metal-mediated cyclization of enynes to give dienes, see: Aubert, C.; Buisine, O.; Malacria, M. Chem. Rev. 2002, 102, 813-834.
    • (2002) Chem. Rev. , vol.102 , pp. 813-834
    • Aubert, C.1    Buisine, O.2    Malacria, M.3
  • 21
    • 0001170349 scopus 로고
    • For tungsten-mediated intramolecular PK reactions of α,β-unsaturated esters and nitriles, see: (a) Shiu, Y.-T.; Madhushaw, R. J.; Li, W.-T.; Lin, Y.-C.; Lee, G.-H.; Peng, S.-M.; Liao, F. L.; Wang, S.-L.; Liu, R. S. J. Am. Chem. Soc. 1999, 121, 4066-4067. (b) Hoye, T. R.; Suriano, J. A. J. Am. Chem. Soc. 1993, 115, 1154-1156.
    • (1993) J. Am. Chem. Soc. , vol.115 , pp. 1154-1156
    • Hoye, T.R.1    Suriano, J.A.2
  • 24
    • 0242642965 scopus 로고    scopus 로고
    • Note: Unlike this behavior, Cazes et al. have reported some successful N-oxide-promoted intermolecular PK reactions (see ref 6a)
    • Unlike this behavior, Cazes et al. have reported some successful N-oxide-promoted intermolecular PK reactions (see ref 6a).
  • 27
    • 0242391199 scopus 로고    scopus 로고
    • 6, 80 °C; 72% yield] and further OH protection
    • 6, 80 °C; 72% yield] and further OH protection.
  • 30
    • 0242558277 scopus 로고    scopus 로고
    • 6 in trans arrangement)
    • 6 in trans arrangement).
  • 31
    • 0034613217 scopus 로고    scopus 로고
    • Intramolecular PK reactions of enynes substituted at the allylic and propargylic position tend to be highly exo-selective. See, for instance: (a) Mukai, C.; Sonobe, H.; Kim, J. S.; Hanoka, M. J. Org. Chem. 2000, 65, 6654-6659. (b) Mukai, C.; Kim, J. S.; Sonobe, H.; Hanaoka, M. J. Org. Chem. 1999, 64, 6822-6832. (c) Magnus, P.; Principe, L. M.; Slater, M. J. J. Org. Chem. 1987, 52, 1483-1486. (d) Magnus, P.; Principe, L. M. Tetrahedron Lett. 1985, 26, 4851-4854. For endo-selective intramolecular PK reactions of α,β-unsaturated sulfones, see ref 8.
    • (2000) J. Org. Chem. , vol.65 , pp. 6654-6659
    • Mukai, C.1    Sonobe, H.2    Kim, J.S.3    Hanoka, M.4
  • 32
    • 0344117715 scopus 로고    scopus 로고
    • Intramolecular PK reactions of enynes substituted at the allylic and propargylic position tend to be highly exo-selective. See, for instance: (a) Mukai, C.; Sonobe, H.; Kim, J. S.; Hanoka, M. J. Org. Chem. 2000, 65, 6654-6659. (b) Mukai, C.; Kim, J. S.; Sonobe, H.; Hanaoka, M. J. Org. Chem. 1999, 64, 6822-6832. (c) Magnus, P.; Principe, L. M.; Slater, M. J. J. Org. Chem. 1987, 52, 1483-1486. (d) Magnus, P.; Principe, L. M. Tetrahedron Lett. 1985, 26, 4851-4854. For endo-selective intramolecular PK reactions of α,β-unsaturated sulfones, see ref 8.
    • (1999) J. Org. Chem. , vol.64 , pp. 6822-6832
    • Mukai, C.1    Kim, J.S.2    Sonobe, H.3    Hanaoka, M.4
  • 33
    • 0023222798 scopus 로고
    • Intramolecular PK reactions of enynes substituted at the allylic and propargylic position tend to be highly exo-selective. See, for instance: (a) Mukai, C.; Sonobe, H.; Kim, J. S.; Hanoka, M. J. Org. Chem. 2000, 65, 6654-6659. (b) Mukai, C.; Kim, J. S.; Sonobe, H.; Hanaoka, M. J. Org. Chem. 1999, 64, 6822-6832. (c) Magnus, P.; Principe, L. M.; Slater, M. J. J. Org. Chem. 1987, 52, 1483-1486. (d) Magnus, P.; Principe, L. M. Tetrahedron Lett. 1985, 26, 4851-4854. For endo-selective intramolecular PK reactions of α,β-unsaturated sulfones, see ref 8.
    • (1987) J. Org. Chem. , vol.52 , pp. 1483-1486
    • Magnus, P.1    Principe, L.M.2    Slater, M.J.3
  • 34
    • 1442266343 scopus 로고
    • Intramolecular PK reactions of enynes substituted at the allylic and propargylic position tend to be highly exo-selective. See, for instance: (a) Mukai, C.; Sonobe, H.; Kim, J. S.; Hanoka, M. J. Org. Chem. 2000, 65, 6654-6659. (b) Mukai, C.; Kim, J. S.; Sonobe, H.; Hanaoka, M. J. Org. Chem. 1999, 64, 6822-6832. (c) Magnus, P.; Principe, L. M.; Slater, M. J. J. Org. Chem. 1987, 52, 1483-1486. (d) Magnus, P.; Principe, L. M. Tetrahedron Lett. 1985, 26, 4851-4854. For endo-selective intramolecular PK reactions of α,β-unsaturated sulfones, see ref 8.
    • (1985) Tetrahedron Lett. , vol.26 , pp. 4851-4854
    • Magnus, P.1    Principe, L.M.2
  • 36
    • 0242642964 scopus 로고    scopus 로고
    • Note: Stereochemical assignment of products 4i,j and 3j,n was based on NMR spectroscopic analysis (NOESY experiments)
    • Stereochemical assignment of products 4i,j and 3j,n was based on NMR spectroscopic analysis (NOESY experiments).


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