메뉴 건너뛰기




Volumn 6, Issue 24, 2004, Pages 4543-4546

Ruthenium-catalyzed [2 + 2] cycloadditions between bicyclic alkenes and alkynyl halides

Author keywords

[No Author keywords available]

Indexed keywords

ALKENE DERIVATIVE; ALKYNYL GROUP; BICYCLO COMPOUND; HALIDE; NORBORNADIENE DERIVATIVE; RUTHENIUM;

EID: 10044224654     PISSN: 15237060     EISSN: None     Source Type: Journal    
DOI: 10.1021/ol048111g     Document Type: Article
Times cited : (69)

References (45)
  • 1
    • 0002110351 scopus 로고    scopus 로고
    • For reviews on transition metal-catalyzed cycloadditions, see: (a) Lautens, M.; Klute, W.; Tam, W. Chem. Rev. 1996, 96, 49. (b) Hegedus, L. S. Coord. Chem. Rev. 1997, 161, 129. (c) Wender, P. A.; Love, J. A. In Advances in Cycloaddition; JAI Press: Greenwich, 1999; Vol. 5, pp 1-45.
    • (1996) Chem. Rev. , vol.96 , pp. 49
    • Lautens, M.1    Klute, W.2    Tam, W.3
  • 2
    • 0031138748 scopus 로고    scopus 로고
    • For reviews on transition metal-catalyzed cycloadditions, see: (a) Lautens, M.; Klute, W.; Tam, W. Chem. Rev. 1996, 96, 49. (b) Hegedus, L. S. Coord. Chem. Rev. 1997, 161, 129. (c) Wender, P. A.; Love, J. A. In Advances in Cycloaddition; JAI Press: Greenwich, 1999; Vol. 5, pp 1-45.
    • (1997) Coord. Chem. Rev. , vol.161 , pp. 129
    • Hegedus, L.S.1
  • 3
    • 0002408267 scopus 로고    scopus 로고
    • JAI Press: Greenwich
    • For reviews on transition metal-catalyzed cycloadditions, see: (a) Lautens, M.; Klute, W.; Tam, W. Chem. Rev. 1996, 96, 49. (b) Hegedus, L. S. Coord. Chem. Rev. 1997, 161, 129. (c) Wender, P. A.; Love, J. A. In Advances in Cycloaddition; JAI Press: Greenwich, 1999; Vol. 5, pp 1-45.
    • (1999) Advances in Cycloaddition , vol.5 , pp. 1-45
    • Wender, P.A.1    Love, J.A.2
  • 4
    • 0036296873 scopus 로고    scopus 로고
    • For recent reviews on transition metal-catalyzed [2 + 2 + 1] cycloadditions, see: (a) Pericas, M. A.; Balsells, J.; Castro, J.; Marchueta, I.; Moyano, A.; Riera, A.; Vazquez, J.; Verdaguer, X. Pure Appl. Chem. 2002, 74, 167. (b) Sugihara, T.; Yamaguchi, M.; Nishizawa, M. Chem. Eur. J. 2001, 7, 1589. (c) Brummond, K. M.; Kent, J. L. Tetrahedron 2000, 56, 3263. (d) Buchwald, S. L.; Hicks, F. A. In Comprehensive Asymmetric Catalysis I-III, Jabosen, E. N., Pfaltz, A., Yamamoto, H., Eds.; Springer-Verlag: Berlin, 1999; Vol. 2, pp 491-510. (e) Keun Chung, Y. Coor. Chem. Rev. 1999, 188, 297.
    • (2002) Pure Appl. Chem. , vol.74 , pp. 167
    • Pericas, M.A.1    Balsells, J.2    Castro, J.3    Marchueta, I.4    Moyano, A.5    Riera, A.6    Vazquez, J.7    Verdaguer, X.8
  • 5
    • 0035901654 scopus 로고    scopus 로고
    • For recent reviews on transition metal-catalyzed [2 + 2 + 1] cycloadditions, see: (a) Pericas, M. A.; Balsells, J.; Castro, J.; Marchueta, I.; Moyano, A.; Riera, A.; Vazquez, J.; Verdaguer, X. Pure Appl. Chem. 2002, 74, 167. (b) Sugihara, T.; Yamaguchi, M.; Nishizawa, M. Chem. Eur. J. 2001, 7, 1589. (c) Brummond, K. M.; Kent, J. L. Tetrahedron 2000, 56, 3263. (d) Buchwald, S. L.; Hicks, F. A. In Comprehensive Asymmetric Catalysis I-III, Jabosen, E. N., Pfaltz, A., Yamamoto, H., Eds.; Springer-Verlag: Berlin, 1999; Vol. 2, pp 491-510. (e) Keun Chung, Y. Coor. Chem. Rev. 1999, 188, 297.
    • (2001) Chem. Eur. J. , vol.7 , pp. 1589
    • Sugihara, T.1    Yamaguchi, M.2    Nishizawa, M.3
  • 6
    • 0034686072 scopus 로고    scopus 로고
    • For recent reviews on transition metal-catalyzed [2 + 2 + 1] cycloadditions, see: (a) Pericas, M. A.; Balsells, J.; Castro, J.; Marchueta, I.; Moyano, A.; Riera, A.; Vazquez, J.; Verdaguer, X. Pure Appl. Chem. 2002, 74, 167. (b) Sugihara, T.; Yamaguchi, M.; Nishizawa, M. Chem. Eur. J. 2001, 7, 1589. (c) Brummond, K. M.; Kent, J. L. Tetrahedron 2000, 56, 3263. (d) Buchwald, S. L.; Hicks, F. A. In Comprehensive Asymmetric Catalysis I-III, Jabosen, E. N., Pfaltz, A., Yamamoto, H., Eds.; Springer-Verlag: Berlin, 1999; Vol. 2, pp 491-510. (e) Keun Chung, Y. Coor. Chem. Rev. 1999, 188, 297.
    • (2000) Tetrahedron , vol.56 , pp. 3263
    • Brummond, K.M.1    Kent, J.L.2
  • 7
    • 0001216151 scopus 로고    scopus 로고
    • Jabosen, E. N., Pfaltz, A., Yamamoto, H., Eds.; Springer-Verlag: Berlin
    • For recent reviews on transition metal-catalyzed [2 + 2 + 1] cycloadditions, see: (a) Pericas, M. A.; Balsells, J.; Castro, J.; Marchueta, I.; Moyano, A.; Riera, A.; Vazquez, J.; Verdaguer, X. Pure Appl. Chem. 2002, 74, 167. (b) Sugihara, T.; Yamaguchi, M.; Nishizawa, M. Chem. Eur. J. 2001, 7, 1589. (c) Brummond, K. M.; Kent, J. L. Tetrahedron 2000, 56, 3263. (d) Buchwald, S. L.; Hicks, F. A. In Comprehensive Asymmetric Catalysis I-III, Jabosen, E. N., Pfaltz, A., Yamamoto, H., Eds.; Springer-Verlag: Berlin, 1999; Vol. 2, pp 491-510. (e) Keun Chung, Y. Coor. Chem. Rev. 1999, 188, 297.
    • (1999) Comprehensive Asymmetric Catalysis I-III , vol.2 , pp. 491-510
    • Buchwald, S.L.1    Hicks, F.A.2
  • 8
    • 0000939078 scopus 로고    scopus 로고
    • For recent reviews on transition metal-catalyzed [2 + 2 + 1] cycloadditions, see: (a) Pericas, M. A.; Balsells, J.; Castro, J.; Marchueta, I.; Moyano, A.; Riera, A.; Vazquez, J.; Verdaguer, X. Pure Appl. Chem. 2002, 74, 167. (b) Sugihara, T.; Yamaguchi, M.; Nishizawa, M. Chem. Eur. J. 2001, 7, 1589. (c) Brummond, K. M.; Kent, J. L. Tetrahedron 2000, 56, 3263. (d) Buchwald, S. L.; Hicks, F. A. In Comprehensive Asymmetric Catalysis I-III, Jabosen, E. N., Pfaltz, A., Yamamoto, H., Eds.; Springer-Verlag: Berlin, 1999; Vol. 2, pp 491-510. (e) Keun Chung, Y. Coor. Chem. Rev. 1999, 188, 297.
    • (1999) Coor. Chem. Rev. , vol.188 , pp. 297
    • Keun Chung, Y.1
  • 34
    • 0026741042 scopus 로고
    • For selected examples of transition metal-catalyzed reaction involving alkynyl halides, see: (a) Beaudet, L; Parrain, J.-L.; Quintard J.-P. Tetrahedron Lett. 1992, 33, 3647. (b) Bouyssi, D.; Gore, J.; Balme, G. Tetrahedron Lett. 1992, 33, 2811. (c) Weigelt, M.; Becher, D.; Poetsch, E.; Bruhn, C.; Ströhl, D.; Steinborn D. J. Prakt. Chem. 1999, 341, 477. (d) Abele, E.; Rubina, K.; Fleisher, M.; Popelis, J.; Arsenyan, P.; Lukecics, E. Appl. Organomet. Chem. 2002, 16, 141.
    • (1992) Tetrahedron Lett. , vol.33 , pp. 3647
    • Beaudet, L.1    Parrain, J.-L.2    Quintard, J.-P.3
  • 35
    • 0026623032 scopus 로고
    • For selected examples of transition metal-catalyzed reaction involving alkynyl halides, see: (a) Beaudet, L; Parrain, J.-L.; Quintard J.-P. Tetrahedron Lett. 1992, 33, 3647. (b) Bouyssi, D.; Gore, J.; Balme, G. Tetrahedron Lett. 1992, 33, 2811. (c) Weigelt, M.; Becher, D.; Poetsch, E.; Bruhn, C.; Ströhl, D.; Steinborn D. J. Prakt. Chem. 1999, 341, 477. (d) Abele, E.; Rubina, K.; Fleisher, M.; Popelis, J.; Arsenyan, P.; Lukecics, E. Appl. Organomet. Chem. 2002, 16, 141.
    • (1992) Tetrahedron Lett. , vol.33 , pp. 2811
    • Bouyssi, D.1    Gore, J.2    Balme, G.3
  • 36
    • 0347155093 scopus 로고    scopus 로고
    • For selected examples of transition metal-catalyzed reaction involving alkynyl halides, see: (a) Beaudet, L; Parrain, J.-L.; Quintard J.-P. Tetrahedron Lett. 1992, 33, 3647. (b) Bouyssi, D.; Gore, J.; Balme, G. Tetrahedron Lett. 1992, 33, 2811. (c) Weigelt, M.; Becher, D.; Poetsch, E.; Bruhn, C.; Ströhl, D.; Steinborn D. J. Prakt. Chem. 1999, 341, 477. (d) Abele, E.; Rubina, K.; Fleisher, M.; Popelis, J.; Arsenyan, P.; Lukecics, E. Appl. Organomet. Chem. 2002, 16, 141.
    • (1999) J. Prakt. Chem. , vol.341 , pp. 477
    • Weigelt, M.1    Becher, D.2    Poetsch, E.3    Bruhn, C.4    Ströhl, D.5    Steinborn, D.6
  • 37
    • 0036292753 scopus 로고    scopus 로고
    • For selected examples of transition metal-catalyzed reaction involving alkynyl halides, see: (a) Beaudet, L; Parrain, J.-L.; Quintard J.-P. Tetrahedron Lett. 1992, 33, 3647. (b) Bouyssi, D.; Gore, J.; Balme, G. Tetrahedron Lett. 1992, 33, 2811. (c) Weigelt, M.; Becher, D.; Poetsch, E.; Bruhn, C.; Ströhl, D.; Steinborn D. J. Prakt. Chem. 1999, 341, 477. (d) Abele, E.; Rubina, K.; Fleisher, M.; Popelis, J.; Arsenyan, P.; Lukecics, E. Appl. Organomet. Chem. 2002, 16, 141.
    • (2002) Appl. Organomet. Chem. , vol.16 , pp. 141
    • Abele, E.1    Rubina, K.2    Fleisher, M.3    Popelis, J.4    Arsenyan, P.5    Lukecics, E.6
  • 41
    • 0006101030 scopus 로고
    • (b) For the preparation of 10a, see: Viehe, H. G. Chem. Ber. 1959, 92, 1950.
    • (1959) Chem. Ber. , vol.92 , pp. 1950
    • Viehe, H.G.1
  • 42
    • 10044288990 scopus 로고    scopus 로고
    • see ref 13
    • (c) For a general procedure for the preparation of alkynyl iodides, see ref 13.
  • 43
    • 10044251842 scopus 로고    scopus 로고
    • note
    • When 12 was reduced with lithium alminium hydride or treated with tert-butyllithium followed by a quench with methanol, the loss of iodide was observed.
  • 44
    • 10044229142 scopus 로고    scopus 로고
    • note
    • The exo stereochemistry of both groups was established by GOESY NMR experiments of product 13, which was obtained through the same conditions using norbornene instead of norbornadiene. Compound 13 could also be prepared by hydrogenation of 12.


* 이 정보는 Elsevier사의 SCOPUS DB에서 KISTI가 분석하여 추출한 것입니다.