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Volumn 10, Issue 5, 2008, Pages 925-928

Synthesis of functionalized oxazolones by a sequence of Cu(ll)- And Au(l)-catalyzed transformations

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EID: 51049083425     PISSN: 15237060     EISSN: None     Source Type: Journal    
DOI: 10.1021/ol703077g     Document Type: Article
Times cited : (130)

References (57)
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    • For selected examples, see: With phosgene (a) Hamad, M. O.; Kiptoo, P. K.; Stinchcomb, A. L.; Crooks, P. Bioorg. Med. Chem. 2006, 14, 7051-7061. With triphosgene
    • For selected examples, see: With phosgene (a) Hamad, M. O.; Kiptoo, P. K.; Stinchcomb, A. L.; Crooks, P. Bioorg. Med. Chem. 2006, 14, 7051-7061. With triphosgene
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    • For recent reviews on gold catalysis, see: a
    • For recent reviews on gold catalysis, see: (a) Gorin, D. J.; Toste, F. D. Nature 2007, 46, 395 - 403.
    • (2007) Nature , vol.46 , pp. 395-403
    • Gorin, D.J.1    Toste, F.D.2
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    • For selected examples, see: Furans (a) Hashmi, A. S. K.; Schwarz, L.; Choi, J.-H.; Frost, T. M. Angew. Chem., Int. Ed. 2000, 39, 2285-2289.
    • For selected examples, see: Furans (a) Hashmi, A. S. K.; Schwarz, L.; Choi, J.-H.; Frost, T. M. Angew. Chem., Int. Ed. 2000, 39, 2285-2289.
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    • Oxazoles and oxazolines
    • (e)Istrate, F.; Gagosz, F. J. Org. Chem. 2007, 73, 730-733. Oxazoles and oxazolines
    • (2007) J. Org. Chem , vol.73 , pp. 730-733
    • Istrate, F.1    Gagosz, F.2
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    • Kang, J. E.; Kim, H.-B.; Lee, J.-W.; Shin, S. Org. Lett. 2006, 8, 3537 - 3540. Lactones and furanones
    • (i)Kang, J. E.; Kim, H.-B.; Lee, J.-W.; Shin, S. Org. Lett. 2006, 8, 3537 - 3540. Lactones and furanones
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    • (c)Kang, J;-E.; Shin, S. Synlett 2006, 717-720.
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    • For leading references dealing with the Cu(II)-catalyzed coupling of bromoalkynes with carbamates, see: (a) Zhang, X.; Zhang, Y.; Huang, J.; Hsung, R. P.; Kurtz, K. C. M.; Oppenheimer, J.; Petersen, M. E.; Sagamanove, I. K.; Shen, L.; Tracey, M. R. J. Org. Chem. 2006, 71, 4170-4177.
    • For leading references dealing with the Cu(II)-catalyzed coupling of bromoalkynes with carbamates, see: (a) Zhang, X.; Zhang, Y.; Huang, J.; Hsung, R. P.; Kurtz, K. C. M.; Oppenheimer, J.; Petersen, M. E.; Sagamanove, I. K.; Shen, L.; Tracey, M. R. J. Org. Chem. 2006, 71, 4170-4177.
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    • Hashmi, A. S. K.; Salathé, R.; Frey, W. Synlett 2007, 1763-1766. For another gold-catalyzed transformation of alkynylamides, see: Couty, S.; Meyer, C. Cossy, J. Angew. Chem., Int. Ed. 2006, 45, 6726-6730.
    • Hashmi, A. S. K.; Salathé, R.; Frey, W. Synlett 2007, 1763-1766. For another gold-catalyzed transformation of alkynylamides, see: Couty, S.; Meyer, C. Cossy, J. Angew. Chem., Int. Ed. 2006, 45, 6726-6730.
  • 52
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    • The reaction reported by Hashmi and coworkers (ref 16) was limited to the use of substrates 3 bearing a hydrogen or a silyl group on the akyne and another electron-withdrawing group Boc
    • The reaction reported by Hashmi and coworkers (ref 16) was limited to the use of substrates 3 bearing a hydrogen or a silyl group on the akyne and another electron-withdrawing group (Boc, Ts, Piv) on the nitrogen atom.
    • Ts, Piv) on the nitrogen atom
  • 53
    • 58149184295 scopus 로고    scopus 로고
    • The poor yields obtained in the case of 3e and 3h may be attributed to a greater steric hindrance around the nitrogen center.
    • The poor yields obtained in the case of 3e and 3h may be attributed to a greater steric hindrance around the nitrogen center.
  • 56
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    • 6) did promote the reaction (53%, 64%) but their efficiency proved limited to a few substrates (see eqs 1 and 2).
    • 6) did promote the reaction (53%, 64%) but their efficiency proved limited to a few substrates (see eqs 1 and 2).
  • 57
    • 58149193814 scopus 로고    scopus 로고
    • 1H NMR on the crude reaction mixture.
    • 1H NMR on the crude reaction mixture.


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