메뉴 건너뛰기




Volumn 48, Issue 30, 2009, Pages 5505-5508

Highly substituted furo[3, 4-d][1, 2]oxazines: Gold-catalyzed regiospecific and diastereoselective 1, 3-dipolar cycloaddition of 2-(1-alkynyl)-2-alken-1- ones with nitrones

Author keywords

Chemoselectivity; Cyclization; Gold; Regioselectivity; Stereoselectivity

Indexed keywords

1 ,3-DIPOLARCYCLOADDITION; ALKYNYLS; CHEMOSELECTIVE; CHEMOSELECTIVITY; DIASTEREOSELECTIVE; DIPOLAR CYCLOADDITIONS; NITRONES; REGIOSPECIFIC; STEREO-SELECTIVE;

EID: 70349782201     PISSN: 14337851     EISSN: None     Source Type: Journal    
DOI: 10.1002/anie.200901299     Document Type: Article
Times cited : (171)

References (78)
  • 5
    • 42049119869 scopus 로고    scopus 로고
    • X. L. Hou, Z. Yang, K.-S. Yeung, H. N. C. Wong in Progress in Heterocyclic Chemistry, 19 (Eds.: G. W. Gribble, J. Joule), Pergamon, Oxford, 2008, pp. 176-207. For selected recent examples, see:
    • X. L. Hou, Z. Yang, K.-S. Yeung, H. N. C. Wong in Progress in Heterocyclic Chemistry, Vol. 19 (Eds.: G. W. Gribble, J. Joule), Pergamon, Oxford, 2008, pp. 176-207. For selected recent examples, see:
  • 9
  • 12
  • 15
    • 0001459493 scopus 로고    scopus 로고
    • Only a very few examples on approach to 3-4 fused bicyclic furans have been reported, see: a M. Suzuki, H. Ohtake, Y. Kameya, N. Hamanaka, R. Noyori, J. Org. Chem. 1989, 54, 5292;
    • Only a very few examples on approach to 3-4 fused bicyclic furans have been reported, see: a) M. Suzuki, H. Ohtake, Y. Kameya, N. Hamanaka, R. Noyori, J. Org. Chem. 1989, 54, 5292;
  • 23
  • 25
  • 30
  • 31
    • 84944032692 scopus 로고    scopus 로고
    • For reviews on synthesis of 1, 2-oxazines, see: a, Elsevier, Oxford, UK, and
    • For reviews on synthesis of 1, 2-oxazines, see: a) T. L. Gilchrist, J. E. Wood in Comprehensive Heterocyclic Chemistry II, Vol. 6, Elsevier, Oxford, UK, 1996, pp. 279-299 and 1177-1307;
    • (1996) Comprehensive Heterocyclic Chemistry II , vol.6
    • Gilchrist, T.L.1    Wood, J.E.2
  • 32
    • 0036602415 scopus 로고    scopus 로고
    • for the synthesis of 1, 2-oxazines, see
    • P. G. Tsoungas, Heterocycles 2002, 57, 1149; for the synthesis of 1, 2-oxazines, see:
    • (2002) Heterocycles , vol.57 , pp. 1149
    • Tsoungas, P.G.1
  • 42
    • 29144485901 scopus 로고    scopus 로고
    • and references cited therein
    • Angew Chem. Int. Ed. 2005, 44, 7832, and references cited therein.
    • (2005) Angew Chem. Int. Ed , vol.44 , pp. 7832
  • 44
  • 45
    • 9344248075 scopus 로고    scopus 로고
    • for the total synthesis of, phyllantidine and nakadomarin A from a cyclopropane, see
    • M. D. Ganton, M. A. Kerr, J. Org. Chem. 2004, 69, 8554; for the total synthesis of (+) - phyllantidine and nakadomarin A from a cyclopropane, see:
    • (2004) J. Org. Chem , vol.69 , pp. 8554
    • Ganton, M.D.1    Kerr, M.A.2
  • 47
  • 51
  • 53
  • 54
    • 53849109140 scopus 로고    scopus 로고
    • For work from our group, see: a
    • For work from our group, see: a) Y. Xiao, J. Zhang, Angew. Chem. 2008, 120, 1929
    • (2008) Angew. Chem , vol.120 , pp. 1929
    • Xiao, Y.1    Zhang, J.2
  • 55
  • 58
    • 4544255270 scopus 로고    scopus 로고
    • Y Xiao, J. Zhang, Chem. Commun. 2009, 3594. [11] a T. Yao, X. Zhang, R. C. Larock, J. Am. Chem. Soc. 2004, 126, 11164;
    • Y Xiao, J. Zhang, Chem. Commun. 2009, 3594. [11] a) T. Yao, X. Zhang, R. C. Larock, J. Am. Chem. Soc. 2004, 126, 11164;
  • 62
    • 70349964900 scopus 로고    scopus 로고
    • For a review on [3+2] cycloaddition of nitrone with olefin, see: a P. N. Confalone, E. M. Huie, Org. React. 1988, 36.
    • For a review on [3+2] cycloaddition of nitrone with olefin, see: a) P. N. Confalone, E. M. Huie, Org. React. 1988, 36.
  • 63
    • 51049121927 scopus 로고    scopus 로고
    • For reviews on gold-catalyzed reactions published since 2008, see: a Z. Li, C. Brouwer, C. He, Chem. Rev. 2008, 108, 3239;
    • For reviews on gold-catalyzed reactions published since 2008, see: a) Z. Li, C. Brouwer, C. He, Chem. Rev. 2008, 108, 3239;
  • 64
  • 71
  • 75
  • 76
    • 70349936645 scopus 로고    scopus 로고
    • Please find the X-ray structures of 5aa and 5da in Figure 1 of the Supporting Information. CCDC 716897 (5aa) and 716897 (5da) contain the supplementary crystallographic data for this paper. These data can be obtained free of charge from The Cambridge Crystallographic Data Centre via www.ccdc.cam.ac.uk/data-request/cif.
    • Please find the X-ray structures of 5aa and 5da in Figure 1 of the Supporting Information. CCDC 716897 (5aa) and 716897 (5da) contain the supplementary crystallographic data for this paper. These data can be obtained free of charge from The Cambridge Crystallographic Data Centre via www.ccdc.cam.ac.uk/data-request/cif.


* 이 정보는 Elsevier사의 SCOPUS DB에서 KISTI가 분석하여 추출한 것입니다.