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Volumn 9, Issue , 2013, Pages 818-826

Gold-catalyzed oxycyclization of allenic carbamates: Expeditious synthesis of 1,3-oxazin-2-ones

Author keywords

Allenes; Computational chemistry; Gold; Gold catalysis; Heterocycles; Reaction mechanisms

Indexed keywords


EID: 84877278057     PISSN: None     EISSN: 18605397     Source Type: Journal    
DOI: 10.3762/bjoc.9.93     Document Type: Article
Times cited : (29)

References (79)
  • 1
    • 33745450775 scopus 로고    scopus 로고
    • Gold-catalyzed synthesis of alkylidene 2-oxazolidinones and 1,3-oxazin-2-ones
    • DOI 10.1021/jo060520y
    • Robles-Machín, R.; Adrio, J.; Carretero, J. C. J. Org. Chem. 2006, 71, 5023. doi:10.1021/jo060520y See for the synthesis of oxazinones from N-Boc-(3-butyn)-1-amines. (Pubitemid 43955787)
    • (2006) Journal of Organic Chemistry , vol.71 , Issue.13 , pp. 5023-5026
    • Robles-Machin, R.1    Adrio, J.2    Carretero, J.C.3
  • 15
    • 84858780394 scopus 로고    scopus 로고
    • doi:10.1002/anie.201101460
    • Yu, S.; Ma, S. Angew. Chem., Int. Ed. 2012, 51, 3074. doi:10.1002/anie.201101460
    • (2012) Angew. Chem., Int. Ed. , vol.51 , pp. 3074
    • Yu, S.1    Ma, S.2
  • 17
    • 79952686693 scopus 로고    scopus 로고
    • doi:10.1021/cr1004088
    • Krause, N.; Winter, C. Chem. Rev. 2011, 111, 1994. doi:10.1021/cr1004088
    • (2011) Chem. Rev. , vol.111 , pp. 1994
    • Krause, N.1    Winter, C.2
  • 18
    • 82955240861 scopus 로고    scopus 로고
    • doi:10.1002/tcr.201100011
    • Alcaide, B.; Almendros, P. Chem. Rec. 2011, 11, 311. doi:10.1002/tcr. 201100011
    • (2011) Chem. Rec. , vol.11 , pp. 311
    • Alcaide, B.1    Almendros, P.2
  • 22
    • 22944485617 scopus 로고    scopus 로고
    • Some typical advances in the synthetic applications of allenes
    • DOI 10.1021/cr020024j
    • Ma, S. Chem. Rev. 2005, 105, 2829. doi:10.1021/cr020024j (Pubitemid 41046992)
    • (2005) Chemical Reviews , vol.105 , Issue.7 , pp. 2829-2871
    • Ma, S.1
  • 27
    • 0034675566 scopus 로고    scopus 로고
    • Hashmi, A. S. K. Angew. Chem., Int. Ed. 2000, 39, 3590. doi:10.1002/1521-3773(20001016)39:203590::AID-ANIE3590.3.0.CO;2-L
    • (2000) Angew. Chem., Int. Ed. , vol.39 , pp. 3590
    • Hashmi, A.S.K.1
  • 33
    • 79951861392 scopus 로고    scopus 로고
    • doi:10.1039/c0cs00041h
    • Bandini, M. Chem. Soc. Rev. 2011, 40, 1358. doi:10.1039/c0cs00041h
    • (2011) Chem. Soc. Rev. , vol.40 , pp. 1358
    • Bandini, M.1
  • 34
    • 77954837014 scopus 로고    scopus 로고
    • doi:10.1002/anie.200907078
    • Hashmi, A. S. K. Angew. Chem., Int. Ed. 2010, 49, 5232. doi:10.1002/anie.200907078
    • (2010) Angew. Chem., Int. Ed. , vol.49 , pp. 5232
    • Hashmi, A.S.K.1
  • 37
    • 43549119984 scopus 로고    scopus 로고
    • doi:10.1016/j.tet.2008.04.018
    • Muzart, J. Tetrahedron 2008, 64, 5815. doi:10.1016/j.tet.2008.04.018
    • (2008) Tetrahedron , vol.64 , pp. 5815
    • Muzart, J.1
  • 38
    • 34547510627 scopus 로고    scopus 로고
    • Gold-catalyzed organic reactions
    • DOI 10.1021/cr000436x
    • Hashmi, A. S. K. Chem. Rev. 2007, 107, 3180. doi:10.1021/cr000436x (Pubitemid 47177109)
    • (2007) Chemical Reviews , vol.107 , Issue.7 , pp. 3180-3211
    • Hashmi, A.S.K.1
  • 39
    • 33846207883 scopus 로고    scopus 로고
    • Molecular diversity through gold catalysis with alkynes
    • DOI 10.1039/b612008c
    • Jiménez-Núñez, E.; Echavarren, A. M. Chem. Commun. 2007, 333. doi:10.1039/b612008c (Pubitemid 46105510)
    • (2007) Chemical Communications , Issue.4 , pp. 333-346
    • Jimenez-Nunez, E.1    Echavarren, A.M.2
  • 41
    • 33845247117 scopus 로고    scopus 로고
    • Gold and platinum catalysis of enyne cycloisomerization
    • DOI 10.1002/adsc.200600368
    • Zhang, L.; Sun, J.; Kozmin, S. A. Adv. Synth. Catal. 2006, 348, 2271. doi:10.1002/adsc.200600368 See for a review. (Pubitemid 44865607)
    • (2006) Advanced Synthesis and Catalysis , vol.348 , Issue.16-17 , pp. 2271-2296
    • Zhang, L.1    Sun, J.2    Kozmin, S.A.3
  • 46
    • 67149095011 scopus 로고    scopus 로고
    • doi:10.1021/ol900730w
    • Li, H.; Widenhoefer, R. A. Org. Lett. 2009, 11, 2671. doi:10.1021/ol900730w
    • (2009) Org. Lett. , vol.11 , pp. 2671
    • Li, H.1    Widenhoefer, R.A.2
  • 48
    • 34548732498 scopus 로고    scopus 로고
    • Gold(I)-catalyzed hydroaminative cyclization leading to 2,5-dihydroisoxazole
    • DOI 10.1055/s-2007-985571
    • Yeom, H.-S.; Lee, E.-S.; Shin, S. Synlett 2007, 2292. doi:10.1055/s-2007-985571 (Pubitemid 47436203)
    • (2007) Synlett , Issue.14 , pp. 2292-2294
    • Yeom, H.-S.1    Lee, E.-S.2    Shin, S.3
  • 58
    • 33746803733 scopus 로고    scopus 로고
    • Triazolopeptides: Chirospecific synthesis and cis/trans prolyl ratios of structural isomers
    • DOI 10.1016/j.tet.2006.07.007, PII S0040402006010842
    • Paul, A.; Bittermann, H.; Gmeiner, P. Tetrahedron 2006, 62, 8919. doi:10.1016/j.tet.2006.07.007 We used the Dess-Martin oxidation and the Ohira-Bestmann reagent instead of the reported Swern oxidation and Corey-Fuchs olefination. (Pubitemid 44176082)
    • (2006) Tetrahedron , vol.62 , Issue.38 , pp. 8919-8927
    • Paul, A.1    Bittermann, H.2    Gmeiner, P.3
  • 60
    • 64349105023 scopus 로고    scopus 로고
    • doi:10.1021/jo802391x
    • Kuang, J.; Ma, S. J. Org. Chem. 2009, 74, 1763. doi:10.1021/jo802391x
    • (2009) J. Org. Chem. , vol.74 , pp. 1763
    • Kuang, J.1    Ma, S.2
  • 61
    • 79955028274 scopus 로고    scopus 로고
    • doi:10.2174/092986711795328355 Compounds 3d-1464doi:10.2174/ 092986711795328355 Compf and 4d;-lactam and oxazinone frameworks. See for a review on hybrid chemical entities
    • Decker, M. Curr. Med. Chem. 2011, 18, 1464. doi:10.2174/ 092986711795328355 Compounds 3d-f and 4d-f can be considered as hybrid scaffolds, i.e., as a combination of the biologically relevant β-lactam and oxazinone frameworks. See for a review on hybrid chemical entities.
    • (2011) Curr. Med. Chem. , vol.18 , pp. 1464
    • Decker, M.1
  • 62
    • 77956595560 scopus 로고    scopus 로고
    • doi:10.2174/138955710791608280
    • Tsogoeva, S. B. Mini-Rev. Med. Chem. 2010, 10, 773. doi:10.2174/ 138955710791608280
    • (2010) Mini-Rev. Med. Chem. , vol.10 , pp. 773
    • Tsogoeva, S.B.1
  • 63
    • 38949125112 scopus 로고    scopus 로고
    • doi:10.1021/ar7000843
    • Meunier, B. Acc. Chem. Res. 2008, 41, 69. doi:10.1021/ar7000843
    • (2008) Acc. Chem. Res. , vol.41 , pp. 69
    • Meunier, B.1
  • 65
    • 77955673540 scopus 로고    scopus 로고
    • doi:10.1021/cr900211p Fused tricyclic 34-4489.doi:10.1021/cr900211p Fused tricydihydro;C. Fused indole derivatives are represented in numerous natural alkaloids and synthetic pharmaceuticals, which display a number of interesting biological activities
    • Kochanowska-Karamyan, A. J.; Hamann, M. T. Chem. Rev. 2010, 110, 4489. doi:10.1021/cr900211p Fused tricyclic 3,4-dihydro-2H-1,3-oxazin-2-one 4j was more efficiently obtained by performing the reaction at 80 °C. Fused indole derivatives are represented in numerous natural alkaloids and synthetic pharmaceuticals, which display a number of interesting biological activities.
    • (2010) Chem. Rev. , vol.110 , pp. 4489
    • Kochanowska-Karamyan, A.J.1    Hamann, M.T.2
  • 67
    • 33746864043 scopus 로고    scopus 로고
    • Practical methodologies for the synthesis of indoles
    • DOI 10.1021/cr0505270
    • Humphrey, G. R.; Kuethe, J. T. Chem. Rev. 2006, 106, 2875. doi:10.1021/cr0505270 (Pubitemid 44193050)
    • (2006) Chemical Reviews , vol.106 , Issue.7 , pp. 2875-2911
    • Humphrey, G.R.1    Kuethe, J.T.2
  • 70
    • 79953838868 scopus 로고    scopus 로고
    • doi:10.1002/chem.201003611
    • Shu, W.; Yu, Q.; Jia, G.; Ma, S. Chem.-Eur. J. 2011, 17, 4720. doi:10.1002/chem.201003611
    • (2011) Chem.-Eur. J. , vol.17 , pp. 4720
    • Shu, W.1    Yu, Q.2    Jia, G.3    Ma, S.4
  • 74
    • 58949086723 scopus 로고
    • doi:10.1246/cl.1988.1431 See for the isolation of an allylic gold complex
    • Komiya, S.; Ozaki, S. Chem. Lett. 1988, 17, 1431. doi:10.1246/cl.1988. 1431 See for the isolation of an allylic gold complex.
    • (1988) Chem. Lett. , vol.17 , pp. 1431
    • Komiya, S.1    Ozaki, S.2
  • 75
    • 84877284864 scopus 로고    scopus 로고
    • 1H NMR Of The Reaction Mixtures Revealed The Presence Of 2-methylprop-1-ene Which Is Likely Formed From The Tert-butyl Fragmentation. For Pioneering Work On The Introduction Of Tert-butyl Carbonates As A Cation-trapping Group In Gold Catalysis See References [76-78]
    • 1H NMR of the reaction mixtures revealed the presence of 2-methylprop-1-ene, which is likely formed from the tert-butyl fragmentation. For pioneering work on the introduction of tert-butyl carbonates as a cation-trapping group in gold catalysis, see references [76-78].
  • 76
    • 32644446865 scopus 로고    scopus 로고
    • Gold(I)-catalyzed formation of 4-alkylidene-1,3-dioxolan-2-ones from propargylic tert-butyl carbonates
    • DOI 10.1021/ol053100o
    • Buzas, A.; Gagosz, F. Org. Lett. 2006, 8, 515. doi:10.1021/ol053100o (Pubitemid 43241699)
    • (2006) Organic Letters , vol.8 , Issue.3 , pp. 515-518
    • Buzas, A.1    Gagosz, F.2
  • 77
    • 33645403185 scopus 로고    scopus 로고
    • doi:10.1055/s-2006-933110
    • Kang, J.-E.; Shin, S. Synlett 2006, 717. doi:10.1055/s-2006-933110
    • (2006) Synlett , vol.717
    • Kang, J.-E.1    Shin, S.2
  • 78
    • 31744435555 scopus 로고    scopus 로고
    • doi:10.5012/bkcs.2005.26.12.1925
    • Shin, S.-H. Bull. Korean Chem. Soc. 2005, 26, 1925. doi:10.5012/bkcs. 2005.26.12.1925
    • (2005) Bull. Korean Chem. Soc. , vol.26 , pp. 1925
    • Shin, S.-H.1
  • 79
    • 84877272514 scopus 로고    scopus 로고
    • The corresponding second-order perturbation energy from the NBO method associated with this LP(O) → d(Au) delocalization was computed to be ca. 5 kcal/mol
    • The corresponding second-order perturbation energy from the NBO method associated with this LP(O) → d(Au) delocalization was computed to be ca. 5 kcal/mol.


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