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Volumn , Issue 6, 2008, Pages 911-913

The reaction of α,β-unsaturated sulfones with isobenzofuran and N-Boc-isoindole using Warrener's methodology

Author keywords

Diels Alder reactions; Isobenzofuran; Isoindole; Sulfones; Warrener's reaction

Indexed keywords

BENZOFURAN DERIVATIVE; ISOINDOLE DERIVATIVE; SULFONE DERIVATIVE;

EID: 42049111845     PISSN: 09365214     EISSN: None     Source Type: Journal    
DOI: 10.1055/s-2008-1042934     Document Type: Article
Times cited : (14)

References (43)
  • 1
    • 33744811177 scopus 로고    scopus 로고
    • For reviews on the reaction, synthesis, and applications of benzofurans including isobenzofurans see: a, Gribble, G. W, Joule, J. A, Eds, Pergamon: Oxford, Chap. 5, 192-199
    • For reviews on the reaction, synthesis, and applications of benzofurans including isobenzofurans see: (a) Hou, X. L.; Yang, Z.; Wong, H. N. C. Progress in Heterocyclic Chemistry, Part 3, Vol. 15; Gribble, G. W.; Joule, J. A., Eds.; Pergamon: Oxford, 2003, Chap. 5, 192-199.
    • (2003) Progress in Heterocyclic Chemistry , vol.15 , Issue.PART 3
    • Hou, X.L.1    Yang, Z.2    Wong, H.N.C.3
  • 2
    • 42049118051 scopus 로고    scopus 로고
    • Gribble, G. W, Joule, J. A, Eds, Pergamon: Oxford, Chap. 5, 180-188
    • (b) Hou, X. L.; Yang, Z.; Yeung, K. S.; Wong, H. N. C. Progress in Heterocyclic Chemistry, Part 3, Vol. 16; Gribble, G. W.; Joule, J. A., Eds.; Pergamon: Oxford, 2004, Chap. 5, 180-188.
    • (2004) Progress in Heterocyclic Chemistry , vol.16 , Issue.PART 3
    • Hou, X.L.1    Yang, Z.2    Yeung, K.S.3    Wong, H.N.C.4
  • 3
    • 33744811177 scopus 로고    scopus 로고
    • Gribble, G. W, Joule, J. A, Eds, Pergamon: Oxford, Chap. 5, 158-164
    • (c) Hou, X. L.; Yang, Z.; Yeung, K. S.; Wong, H. N. C. Progress in Heterocyclic Chemistry, Part 3, Vol. 17; Gribble, G. W.; Joule, J. A., Eds.; Pergamon: Oxford, 2005, Chap. 5, 158-164.
    • (2005) Progress in Heterocyclic Chemistry , vol.17 , Issue.PART 3
    • Hou, X.L.1    Yang, Z.2    Yeung, K.S.3    Wong, H.N.C.4
  • 4
    • 42049083155 scopus 로고    scopus 로고
    • Gribble, G. W, Joule, J. A, Eds, Pergamon: Oxford, Chap. 5, 203-210
    • (d) Hou, X. L.; Yang, Z.; Yeung, K. S.; Wong, H. N. C. Progress in Heterocyclic Chemistry, Part 3, Vol. 18; Gribble, G. W.; Joule, J. A., Eds.; Pergamon: Oxford, 2006, Chap. 5, 203-210.
    • (2006) Progress in Heterocyclic Chemistry , vol.18 , Issue.PART 3
    • Hou, X.L.1    Yang, Z.2    Yeung, K.S.3    Wong, H.N.C.4
  • 5
    • 42049119383 scopus 로고    scopus 로고
    • Hou, X. L.; Yang, Z.; Yeung, K. S.; Wong, H. N. C. Progress in Heterocyclic Chemistry, Part 3, 19; Gribble, G. W.; Joule, J. A., Eds.; Pergamon: Oxford, 2007, Chap. 5, 193-200; see also previous issues of this series.
    • (e) Hou, X. L.; Yang, Z.; Yeung, K. S.; Wong, H. N. C. Progress in Heterocyclic Chemistry, Part 3, Vol. 19; Gribble, G. W.; Joule, J. A., Eds.; Pergamon: Oxford, 2007, Chap. 5, 193-200; see also previous issues of this series.
  • 6
    • 0023952038 scopus 로고
    • For a more extensive review on isobenzofuran, including many synthetic applications, see
    • (f) For a more extensive review on isobenzofuran, including many synthetic applications, see: Rodrigo, R. Tetrahedron 1988, 44, 2093.
    • (1988) Tetrahedron , vol.44 , pp. 2093
    • Rodrigo, R.1
  • 7
    • 0000802815 scopus 로고
    • For reviews on the isoindole chemistry, see
    • (g) For reviews on the isoindole chemistry, see: Bounett, R.; North, S. A. Adv. Heterocycl. Chem. 1981, 29, 341.
    • (1981) Adv. Heterocycl. Chem , vol.29 , pp. 341
    • Bounett, R.1    North, S.A.2
  • 9
    • 42049107998 scopus 로고    scopus 로고
    • For methods of generation of IBF excluding Warrener's methodology, see ref. 1f and: (a) Peters, O.; Friedrichsen, W. Trends Heterocycl. Chem. 1995, 4, 217.
    • For methods of generation of IBF excluding Warrener's methodology, see ref. 1f and: (a) Peters, O.; Friedrichsen, W. Trends Heterocycl. Chem. 1995, 4, 217.
  • 14
    • 42049094864 scopus 로고    scopus 로고
    • See also ref. 10
    • (f) See also ref. 10.
  • 15
    • 1842383312 scopus 로고    scopus 로고
    • Isobenzofurans: (a) Warrener, R. N. J. Am. Chem. Soc. 1971, 93, 2346.
    • Isobenzofurans: (a) Warrener, R. N. J. Am. Chem. Soc. 1971, 93, 2346.
  • 19
    • 33646253224 scopus 로고    scopus 로고
    • For the synthesis and isolation of mono- and bisoxadisilole fused isobenzofurans, see: e
    • For the synthesis and isolation of mono- and bisoxadisilole fused isobenzofurans, see: (e) Chen, Y. L.; Hau, Ch. K.; Wang, H.; He, H.; Wong, M. S.; Lee, A. W. M. J. Org. Chem. 2006, 71, 3512.
    • (2006) J. Org. Chem , vol.71 , pp. 3512
    • Chen, Y.L.1    Hau, C.K.2    Wang, H.3    He, H.4    Wong, M.S.5    Lee, A.W.M.6
  • 20
    • 42049097671 scopus 로고    scopus 로고
    • These reactions coupled with 1,3-dipolar cycloaddition reactions constitute the synthetic strategy for the stereocontrolled construction of [n]polynorbornanes structures. For reviews, see: (a) Warrener, R. N.; Butter, O. N.; Russell, R. A. Synlett 1998, 566.
    • These reactions coupled with 1,3-dipolar cycloaddition reactions constitute the synthetic strategy for the stereocontrolled construction of [n]polynorbornanes structures. For reviews, see: (a) Warrener, R. N.; Butter, O. N.; Russell, R. A. Synlett 1998, 566.
  • 25
    • 0001637839 scopus 로고
    • Sulphones in Organic Synthesis
    • Baldwin, J. E, Magnus, P. D, Eds, Pergamon Press: Oxford, Chap. 6, 236-245
    • Simpkins, N. L. In Sulphones in Organic Synthesis; Baldwin, J. E.; Magnus, P. D., Eds.; Tetrahedron Organic Chemistry Series, Pergamon Press: Oxford, 1993, Chap. 6, 236-245.
    • (1993) Tetrahedron Organic Chemistry Series
    • Simpkins, N.L.1
  • 26
    • 0033609760 scopus 로고    scopus 로고
    • See ref. 5, Chap 9 and: Nájera, C.; Yus, M. Tetrahedron 1999, 55, 10547.
    • See ref. 5, Chap 9 and: Nájera, C.; Yus, M. Tetrahedron 1999, 55, 10547.
  • 33
    • 0000316881 scopus 로고
    • For selected accounts, see: a
    • For selected accounts, see: (a) Glass, R. S.; Smith, D. L. J. Org. Chem. 1974, 39, 3712.
    • (1974) J. Org. Chem , vol.39 , pp. 3712
    • Glass, R.S.1    Smith, D.L.2
  • 37
    • 0001484281 scopus 로고    scopus 로고
    • 10b See: (a) Mirsadeghi, S.; Rickborn, B. J. Org. Chem. 1985, 50, 4340.
    • 10b See: (a) Mirsadeghi, S.; Rickborn, B. J. Org. Chem. 1985, 50, 4340.
  • 39
    • 33644689411 scopus 로고    scopus 로고
    • Synthesized according to: Cho, Y. H.; Fayol, A.; Lautens, M. Tetrahedron: Asymmetry 2006, 17, 416.
    • Synthesized according to: Cho, Y. H.; Fayol, A.; Lautens, M. Tetrahedron: Asymmetry 2006, 17, 416.
  • 40
    • 42049097460 scopus 로고    scopus 로고
    • 2, hexane-EtOAc, 7:3).
    • 2, hexane-EtOAc, 7:3).
  • 41
    • 42049083366 scopus 로고    scopus 로고
    • 13C NMR spectra and mass spectral analysis. In the case of compound 7e, spectroscopic data matched with those previously reported. See ref. 10a.
    • 13C NMR spectra and mass spectral analysis. In the case of compound 7e, spectroscopic data matched with those previously reported. See ref. 10a.
  • 42
    • 42049103440 scopus 로고    scopus 로고
    • 2, δ = 3.96 ppm, dt.
    • 2, δ = 3.96 ppm, dt.
  • 43
    • 42049109723 scopus 로고    scopus 로고
    • 2, δ = 4.00 ppm, dt.
    • 2, δ = 4.00 ppm, dt.


* 이 정보는 Elsevier사의 SCOPUS DB에서 KISTI가 분석하여 추출한 것입니다.