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Volumn 11, Issue 10, 2009, Pages 2077-2080

Ruthenium-catalyzed nucleophilic ring-opening reactions of a 3-aza-2-oxabicyclo[2.2.1]hept-5-ene with alcohols

Author keywords

[No Author keywords available]

Indexed keywords

3 AZA 2 OXABICYCLO(2.2.1)HEPT 5 ENE; 3-AZA-2-OXABICYCLO(2.2.1)HEPT-5-ENE; ALCOHOL DERIVATIVE; FUSED HETEROCYCLIC RINGS; RUTHENIUM;

EID: 66149088801     PISSN: 15237060     EISSN: None     Source Type: Journal    
DOI: 10.1021/ol900454q     Document Type: Article
Times cited : (35)

References (57)
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    • For selected examples of ring-opening reactions of 7-oxabicyclo-[2.2.1] heptenes 1, see: (a) Padwa, A.; Wang, Q. J. Org. Chem. 2006, 71, 7391-7402.
  • 11
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    • For selected examples of ring-opening reactions of 7-oxabicyclo-[3.2.1] octenes 2, see: (a) Lautens, M.; Colucci, J. T.; Hiebert, S.; Smith, N. D.; Bouchain, G. Org. Lett. 2002, 4, 1879-1882.
    • For selected examples of ring-opening reactions of 7-oxabicyclo-[3.2.1] octenes 2, see: (a) Lautens, M.; Colucci, J. T.; Hiebert, S.; Smith, N. D.; Bouchain, G. Org. Lett. 2002, 4, 1879-1882.
  • 16
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    • For selected examples of ring-opening reactions of 7-azabicyclo-[2.2.1] heptenes 3, see: (a) Tenaglia, A.; Marc, S. J. Org. Chem. 2008, 73, 1397-1402.
    • For selected examples of ring-opening reactions of 7-azabicyclo-[2.2.1] heptenes 3, see: (a) Tenaglia, A.; Marc, S. J. Org. Chem. 2008, 73, 1397-1402.
  • 19
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    • For selected examples of ring-opening reactions of 2,3-diazabicyclo[2.2. 1]heptenes 4, see: (a) Bournaud, C.; Lecourt, T.; Micouin, L.; Meliet, C.; Agbossou-Niedercorn, F. Eur. J. Org. Chem. 2008, 2298-2302.
    • For selected examples of ring-opening reactions of 2,3-diazabicyclo[2.2. 1]heptenes 4, see: (a) Bournaud, C.; Lecourt, T.; Micouin, L.; Meliet, C.; Agbossou-Niedercorn, F. Eur. J. Org. Chem. 2008, 2298-2302.
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    • For selected examples of our recent studies of Ru-catalyzed [2 + 2] cycloadditions of bicyclic alkenes and alkynes, see: (a) Villeneuve, K.; Tarn, W. Angew. Chem. Int. Ed. 2004, 43, 610-613.
    • For selected examples of our recent studies of Ru-catalyzed [2 + 2] cycloadditions of bicyclic alkenes and alkynes, see: (a) Villeneuve, K.; Tarn, W. Angew. Chem. Int. Ed. 2004, 43, 610-613.
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    • For examples of Rh-catalyzed asymmetric dimerization of oxa-benzonorbornadienes, see: (a) Allen, A, Le Marquand, P, Burton, R, Villeneuve, K, Tarn, W. J. Org. Chem. 2007, 72, 7849-7857
    • For examples of Rh-catalyzed asymmetric dimerization of oxa-benzonorbornadienes, see: (a) Allen, A.; Le Marquand, P.; Burton, R.; Villeneuve, K.; Tarn, W. J. Org. Chem. 2007, 72, 7849-7857.
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    • For reviews, see: Boger, D. L.; Weinreb, S. M. Hetero Diels-Alder Methodology in Organic Synthesis; Academic Press: San Diego, 1987. See also ref Id.
    • For reviews, see: Boger, D. L.; Weinreb, S. M. Hetero Diels-Alder Methodology in Organic Synthesis; Academic Press: San Diego, 1987. See also ref Id.
  • 35
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    • For selected examples of reductive N-O bond cleavage of 3-aza-2-oxabicyclo[2.2.1]heptenes 5, see: (a) Cesario, C.; Tardibono, L. P.; Miller, M. J. J. Org. Chem. 2009, 74, 448-451.
    • For selected examples of reductive N-O bond cleavage of 3-aza-2-oxabicyclo[2.2.1]heptenes 5, see: (a) Cesario, C.; Tardibono, L. P.; Miller, M. J. J. Org. Chem. 2009, 74, 448-451.
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    • For selected examples of oxidative cleavage of the C=C bond of 3-aza-2-oxabicyclo[2.2.1]heptenes 5, see: (a) Nora, G. P.; Miller, M. J.; Mollmann, U. Bioorg. Med. Chem. Lett. 2006, 16, 3966-3970.
    • For selected examples of oxidative cleavage of the C=C bond of 3-aza-2-oxabicyclo[2.2.1]heptenes 5, see: (a) Nora, G. P.; Miller, M. J.; Mollmann, U. Bioorg. Med. Chem. Lett. 2006, 16, 3966-3970.
  • 44
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    • For selected examples of clevage of the C=C bond of 3-aza-2-oxa bicyclo[2.2.1]heptenes 5 by metathesis reactions, see: (a) Calvet, G.; Blanchard, N.; Kouklovsky, C. Org. Lett. 2007, 9, 1485-1488.
    • For selected examples of clevage of the C=C bond of 3-aza-2-oxa bicyclo[2.2.1]heptenes 5 by metathesis reactions, see: (a) Calvet, G.; Blanchard, N.; Kouklovsky, C. Org. Lett. 2007, 9, 1485-1488.
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    • For acid-mediated ring-opening reaction of 3-aza-2-oxa bicyclo-[2.2.1]heptenes 5, see: Muxworthy, J. P.; Wilkinson, J. A.; Procter, G. Tetrahedron Lett. 1995, 36, 7535-7538.
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    • For palladium and Lewis-acid catalyzed ring-opening reactions of 3-aza-2-oxabicyclo[2.2.1]heptenes 5, see: (a) Lee, W.; Kim, K.-H.; Surman, M. D.; Miller, M. J. J. Org. Chem. 2003, 68, 139-149.
    • For palladium and Lewis-acid catalyzed ring-opening reactions of 3-aza-2-oxabicyclo[2.2.1]heptenes 5, see: (a) Lee, W.; Kim, K.-H.; Surman, M. D.; Miller, M. J. J. Org. Chem. 2003, 68, 139-149.
  • 52
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    • For copper-catalyzed Grignard or organozinc nucleophilic ring-opening reactions, see: a
    • For copper-catalyzed Grignard or organozinc nucleophilic ring-opening reactions, see: (a) Pineschi, M.; Moro, F. D.; Crotti, P.; Macchia, F. Pure Appl. Chem. 2006, 78, 463-467.
    • (2006) Pure Appl. Chem , vol.78 , pp. 463-467
    • Pineschi, M.1    Moro, F.D.2    Crotti, P.3    Macchia, F.4
  • 57
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    • The regio-(1,2-cyclopentene vs 1,4-cyclopentene ring-opened products) and stereochemistry (trans vs cis) of the products were confirmed by various 1D and 2D NMR experiments (HCOSY, HSQC, and NOE).
    • The regio-(1,2-cyclopentene vs 1,4-cyclopentene ring-opened products) and stereochemistry (trans vs cis) of the products were confirmed by various 1D and 2D NMR experiments (HCOSY, HSQC, and NOE).


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