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Volumn 121, Issue 4, 1999, Pages 876-877

A novel cycloisomerization of tetraenones: 4+3 Trapping of the Nazarov oxyallyl intermediate [11]

Author keywords

[No Author keywords available]

Indexed keywords

2 HALOCYCLOPENTANONE; 4 PYRONE DERIVATIVE; ALKANONE; UNCLASSIFIED DRUG;

EID: 0033518564     PISSN: 00027863     EISSN: None     Source Type: Journal    
DOI: 10.1021/ja9837001     Document Type: Letter
Times cited : (75)

References (37)
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    • 5b
    • 5b
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    • note
    • (a) The stereochemistry of 7a and 8a was assigned based on close spectral analogy to 7b and 8b. (b) The stereochemistry of 8d was rigorously determined by X-ray diffraction analysis, and that of 8c was assigned based on close spectral analogy to 8d.
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    • Endo and exo refer to the orientation of the diene in relation to the central carbon of the oxyallyl unit. There is some precedent for greater exo/ endo selectivity in intramolecular [4+3]- and [4+4]-cycloadditions: (a) Harmata, M.; Herron, B. F. J. Org. Chem. 1993, 58, 7393. (b) Sieburth, S. McN.; Hiel, G.; Lin, C.-H.; Kuan, D. P. J. Org. Chem. 1994, 59, 80. (c) Sieburth, S. McN.; Chen, J.; Ravindran, K.; Chen, J. J. Am. Chem. Soc. 1996, 118, 10803.
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    • Harmata, M.1    Herron, B.F.2
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    • Endo and exo refer to the orientation of the diene in relation to the central carbon of the oxyallyl unit. There is some precedent for greater exo/ endo selectivity in intramolecular [4+3]- and [4+4]-cycloadditions: (a) Harmata, M.; Herron, B. F. J. Org. Chem. 1993, 58, 7393. (b) Sieburth, S. McN.; Hiel, G.; Lin, C.-H.; Kuan, D. P. J. Org. Chem. 1994, 59, 80. (c) Sieburth, S. McN.; Chen, J.; Ravindran, K.; Chen, J. J. Am. Chem. Soc. 1996, 118, 10803.
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    • Sieburth, S.McN.1    Hiel, G.2    Lin, C.-H.3    Kuan, D.P.4
  • 32
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    • Endo and exo refer to the orientation of the diene in relation to the central carbon of the oxyallyl unit. There is some precedent for greater exo/ endo selectivity in intramolecular [4+3]- and [4+4]-cycloadditions: (a) Harmata, M.; Herron, B. F. J. Org. Chem. 1993, 58, 7393. (b) Sieburth, S. McN.; Hiel, G.; Lin, C.-H.; Kuan, D. P. J. Org. Chem. 1994, 59, 80. (c) Sieburth, S. McN.; Chen, J.; Ravindran, K.; Chen, J. J. Am. Chem. Soc. 1996, 118, 10803.
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