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Volumn 37, Issue 18, 1996, Pages 3145-3148

Synthesis of cyclopentenones: The new catalytic cocyclization reaction of alkyne, alkene, and carbon monoxide employing catalytic Co(acac)2 and NaBH4

Author keywords

[No Author keywords available]

Indexed keywords

CYCLOPENTENONE DERIVATIVE;

EID: 0029928539     PISSN: 00404039     EISSN: None     Source Type: Journal    
DOI: 10.1016/0040-4039(96)00513-8     Document Type: Article
Times cited : (82)

References (45)
  • 1
    • 0040744387 scopus 로고
    • For recent reviews see: Oppolzer, W.; Snieckus, V. Angew. Chem. Int. Ed. Engl. 1978, 17, 476. Trost, B. M. Chem. Soc. Rev. 1982, 11, 141. Ramaiah, M. Synthesis 1984, 529. Paquette, L. A. Top. Curr. Chem. 1984, 11, 119. Paquette, L. A.; Doherty, A. M. Polyquinane Chemistry; Springer Verlag: Berlin, 1987. Hudlicky, T.; Price, J. Chem. Rev. 1989, 89, 1467. Schore, N. E. In Comprehensive Organic Synthesis; Trost, B. M.; Fleming, I. Eds; Pergamon: Oxford 1991, Vol. 5, p 1037. For recent papers see: Sugahara, T.; Ogasawara, K. Tetrahedron Lett. 1996, 37, 205. Asai, T.; Morizawa, Y.; Shimada, T.; Nakayama, T.; Urushihara, M.; Matsumura, Y.; Yasuda, A. Tetrahedron Lett. 1995, 36, 273.
    • (1978) Angew. Chem. Int. Ed. Engl. , vol.17 , pp. 476
    • Oppolzer, W.1    Snieckus, V.2
  • 2
    • 0020436471 scopus 로고
    • For recent reviews see: Oppolzer, W.; Snieckus, V. Angew. Chem. Int. Ed. Engl. 1978, 17, 476. Trost, B. M. Chem. Soc. Rev. 1982, 11, 141. Ramaiah, M. Synthesis 1984, 529. Paquette, L. A. Top. Curr. Chem. 1984, 11, 119. Paquette, L. A.; Doherty, A. M. Polyquinane Chemistry; Springer Verlag: Berlin, 1987. Hudlicky, T.; Price, J. Chem. Rev. 1989, 89, 1467. Schore, N. E. In Comprehensive Organic Synthesis; Trost, B. M.; Fleming, I. Eds; Pergamon: Oxford 1991, Vol. 5, p 1037. For recent papers see: Sugahara, T.; Ogasawara, K. Tetrahedron Lett. 1996, 37, 205. Asai, T.; Morizawa, Y.; Shimada, T.; Nakayama, T.; Urushihara, M.; Matsumura, Y.; Yasuda, A. Tetrahedron Lett. 1995, 36, 273.
    • (1982) Chem. Soc. Rev. , vol.11 , pp. 141
    • Trost, B.M.1
  • 3
    • 85083210739 scopus 로고
    • For recent reviews see: Oppolzer, W.; Snieckus, V. Angew. Chem. Int. Ed. Engl. 1978, 17, 476. Trost, B. M. Chem. Soc. Rev. 1982, 11, 141. Ramaiah, M. Synthesis 1984, 529. Paquette, L. A. Top. Curr. Chem. 1984, 11, 119. Paquette, L. A.; Doherty, A. M. Polyquinane Chemistry; Springer Verlag: Berlin, 1987. Hudlicky, T.; Price, J. Chem. Rev. 1989, 89, 1467. Schore, N. E. In Comprehensive Organic Synthesis; Trost, B. M.; Fleming, I. Eds; Pergamon: Oxford 1991, Vol. 5, p 1037. For recent papers see: Sugahara, T.; Ogasawara, K. Tetrahedron Lett. 1996, 37, 205. Asai, T.; Morizawa, Y.; Shimada, T.; Nakayama, T.; Urushihara, M.; Matsumura, Y.; Yasuda, A. Tetrahedron Lett. 1995, 36, 273.
    • (1984) Synthesis , pp. 529
    • Ramaiah, M.1
  • 4
    • 0002952842 scopus 로고
    • For recent reviews see: Oppolzer, W.; Snieckus, V. Angew. Chem. Int. Ed. Engl. 1978, 17, 476. Trost, B. M. Chem. Soc. Rev. 1982, 11, 141. Ramaiah, M. Synthesis 1984, 529. Paquette, L. A. Top. Curr. Chem. 1984, 11, 119. Paquette, L. A.; Doherty, A. M. Polyquinane Chemistry; Springer Verlag: Berlin, 1987. Hudlicky, T.; Price, J. Chem. Rev. 1989, 89, 1467. Schore, N. E. In Comprehensive Organic Synthesis; Trost, B. M.; Fleming, I. Eds; Pergamon: Oxford 1991, Vol. 5, p 1037. For recent papers see: Sugahara, T.; Ogasawara, K. Tetrahedron Lett. 1996, 37, 205. Asai, T.; Morizawa, Y.; Shimada, T.; Nakayama, T.; Urushihara, M.; Matsumura, Y.; Yasuda, A. Tetrahedron Lett. 1995, 36, 273.
    • (1984) Top. Curr. Chem. , vol.11 , pp. 119
    • Paquette, L.A.1
  • 5
    • 0004154187 scopus 로고
    • Springer Verlag: Berlin
    • For recent reviews see: Oppolzer, W.; Snieckus, V. Angew. Chem. Int. Ed. Engl. 1978, 17, 476. Trost, B. M. Chem. Soc. Rev. 1982, 11, 141. Ramaiah, M. Synthesis 1984, 529. Paquette, L. A. Top. Curr. Chem. 1984, 11, 119. Paquette, L. A.; Doherty, A. M. Polyquinane Chemistry; Springer Verlag: Berlin, 1987. Hudlicky, T.; Price, J. Chem. Rev. 1989, 89, 1467. Schore, N. E. In Comprehensive Organic Synthesis; Trost, B. M.; Fleming, I. Eds; Pergamon: Oxford 1991, Vol. 5, p 1037. For recent papers see: Sugahara, T.; Ogasawara, K. Tetrahedron Lett. 1996, 37, 205. Asai, T.; Morizawa, Y.; Shimada, T.; Nakayama, T.; Urushihara, M.; Matsumura, Y.; Yasuda, A. Tetrahedron Lett. 1995, 36, 273.
    • (1987) Polyquinane Chemistry
    • Paquette, L.A.1    Doherty, A.M.2
  • 6
    • 33845185291 scopus 로고
    • For recent reviews see: Oppolzer, W.; Snieckus, V. Angew. Chem. Int. Ed. Engl. 1978, 17, 476. Trost, B. M. Chem. Soc. Rev. 1982, 11, 141. Ramaiah, M. Synthesis 1984, 529. Paquette, L. A. Top. Curr. Chem. 1984, 11, 119. Paquette, L. A.; Doherty, A. M. Polyquinane Chemistry; Springer Verlag: Berlin, 1987. Hudlicky, T.; Price, J. Chem. Rev. 1989, 89, 1467. Schore, N. E. In Comprehensive Organic Synthesis; Trost, B. M.; Fleming, I. Eds; Pergamon: Oxford 1991, Vol. 5, p 1037. For recent papers see: Sugahara, T.; Ogasawara, K. Tetrahedron Lett. 1996, 37, 205. Asai, T.; Morizawa, Y.; Shimada, T.; Nakayama, T.; Urushihara, M.; Matsumura, Y.; Yasuda, A. Tetrahedron Lett. 1995, 36, 273.
    • (1989) Chem. Rev. , vol.89 , pp. 1467
    • Hudlicky, T.1    Price, J.2
  • 7
    • 0001334715 scopus 로고
    • Trost, B. M.; Fleming, I. Eds; Pergamon: Oxford
    • For recent reviews see: Oppolzer, W.; Snieckus, V. Angew. Chem. Int. Ed. Engl. 1978, 17, 476. Trost, B. M. Chem. Soc. Rev. 1982, 11, 141. Ramaiah, M. Synthesis 1984, 529. Paquette, L. A. Top. Curr. Chem. 1984, 11, 119. Paquette, L. A.; Doherty, A. M. Polyquinane Chemistry; Springer Verlag: Berlin, 1987. Hudlicky, T.; Price, J. Chem. Rev. 1989, 89, 1467. Schore, N. E. In Comprehensive Organic Synthesis; Trost, B. M.; Fleming, I. Eds; Pergamon: Oxford 1991, Vol. 5, p 1037. For recent papers see: Sugahara, T.; Ogasawara, K. Tetrahedron Lett. 1996, 37, 205. Asai, T.; Morizawa, Y.; Shimada, T.; Nakayama, T.; Urushihara, M.; Matsumura, Y.; Yasuda, A. Tetrahedron Lett. 1995, 36, 273.
    • (1991) Comprehensive Organic Synthesis , vol.5 , pp. 1037
    • Schore, N.E.1
  • 8
    • 0030070995 scopus 로고    scopus 로고
    • For recent reviews see: Oppolzer, W.; Snieckus, V. Angew. Chem. Int. Ed. Engl. 1978, 17, 476. Trost, B. M. Chem. Soc. Rev. 1982, 11, 141. Ramaiah, M. Synthesis 1984, 529. Paquette, L. A. Top. Curr. Chem. 1984, 11, 119. Paquette, L. A.; Doherty, A. M. Polyquinane Chemistry; Springer Verlag: Berlin, 1987. Hudlicky, T.; Price, J. Chem. Rev. 1989, 89, 1467. Schore, N. E. In Comprehensive Organic Synthesis; Trost, B. M.; Fleming, I. Eds; Pergamon: Oxford 1991, Vol. 5, p 1037. For recent papers see: Sugahara, T.; Ogasawara, K. Tetrahedron Lett. 1996, 37, 205. Asai, T.; Morizawa, Y.; Shimada, T.; Nakayama, T.; Urushihara, M.; Matsumura, Y.; Yasuda, A. Tetrahedron Lett. 1995, 36, 273.
    • (1996) Tetrahedron Lett. , vol.37 , pp. 205
    • Sugahara, T.1    Ogasawara, K.2
  • 9
    • 0028814402 scopus 로고
    • For recent reviews see: Oppolzer, W.; Snieckus, V. Angew. Chem. Int. Ed. Engl. 1978, 17, 476. Trost, B. M. Chem. Soc. Rev. 1982, 11, 141. Ramaiah, M. Synthesis 1984, 529. Paquette, L. A. Top. Curr. Chem. 1984, 11, 119. Paquette, L. A.; Doherty, A. M. Polyquinane Chemistry; Springer Verlag: Berlin, 1987. Hudlicky, T.; Price, J. Chem. Rev. 1989, 89, 1467. Schore, N. E. In Comprehensive Organic Synthesis; Trost, B. M.; Fleming, I. Eds; Pergamon: Oxford 1991, Vol. 5, p 1037. For recent papers see: Sugahara, T.; Ogasawara, K. Tetrahedron Lett. 1996, 37, 205. Asai, T.; Morizawa, Y.; Shimada, T.; Nakayama, T.; Urushihara, M.; Matsumura, Y.; Yasuda, A. Tetrahedron Lett. 1995, 36, 273.
    • (1995) Tetrahedron Lett. , vol.36 , pp. 273
    • Asai, T.1    Morizawa, Y.2    Shimada, T.3    Nakayama, T.4    Urushihara, M.5    Matsumura, Y.6    Yasuda, A.7
  • 11
    • 0000213094 scopus 로고
    • (a) Cobalt: Knudsen, M. J. Schore, N. E. J. Org. Chem. 1984, 49, 5025.. Schore, N. E. Chem. Rev. 1988, 88, 989.
    • (1988) Chem. Rev. , vol.88 , pp. 989
    • Schore, N.E.1
  • 12
    • 0000365636 scopus 로고
    • (b) Zirconium: Negishi, E.; Holmes, S. J.; Tour, J. M.; Miller, J. A. J. Am. Chem. Soc. 1985, 107, 2568. Negishi, E.; Cederbaum, F. E.; Takahashi, T. Tetrahedron Lett. 1986, 27, 2829. Buchwald, S. L.; Lum, R. T.; Fisher, R. A.; Davis, W. M. J. Am. Chem. Soc. 1989, 111, 9113. Angel, G.; Owczarczyk, Z.; Negishi, E. Tetrahedron Lett. 1992, 33, 1543.
    • (1985) J. Am. Chem. Soc. , vol.107 , pp. 2568
    • Negishi, E.1    Holmes, S.J.2    Tour, J.M.3    Miller, J.A.4
  • 13
    • 20644436570 scopus 로고
    • (b) Zirconium: Negishi, E.; Holmes, S. J.; Tour, J. M.; Miller, J. A. J. Am. Chem. Soc. 1985, 107, 2568. Negishi, E.; Cederbaum, F. E.; Takahashi, T. Tetrahedron Lett. 1986, 27, 2829. Buchwald, S. L.; Lum, R. T.; Fisher, R. A.; Davis, W. M. J. Am. Chem. Soc. 1989, 111, 9113. Angel, G.; Owczarczyk, Z.; Negishi, E. Tetrahedron Lett. 1992, 33, 1543.
    • (1986) Tetrahedron Lett. , vol.27 , pp. 2829
    • Negishi, E.1    Cederbaum, F.E.2    Takahashi, T.3
  • 14
    • 0024826998 scopus 로고
    • (b) Zirconium: Negishi, E.; Holmes, S. J.; Tour, J. M.; Miller, J. A. J. Am. Chem. Soc. 1985, 107, 2568. Negishi, E.; Cederbaum, F. E.; Takahashi, T. Tetrahedron Lett. 1986, 27, 2829. Buchwald, S. L.; Lum, R. T.; Fisher, R. A.; Davis, W. M. J. Am. Chem. Soc. 1989, 111, 9113. Angel, G.; Owczarczyk, Z.; Negishi, E. Tetrahedron Lett. 1992, 33, 1543.
    • (1989) J. Am. Chem. Soc. , vol.111 , pp. 9113
    • Buchwald, S.L.1    Lum, R.T.2    Fisher, R.A.3    Davis, W.M.4
  • 15
    • 0026548831 scopus 로고
    • (b) Zirconium: Negishi, E.; Holmes, S. J.; Tour, J. M.; Miller, J. A. J. Am. Chem. Soc. 1985, 107, 2568. Negishi, E.; Cederbaum, F. E.; Takahashi, T. Tetrahedron Lett. 1986, 27, 2829. Buchwald, S. L.; Lum, R. T.; Fisher, R. A.; Davis, W. M. J. Am. Chem. Soc. 1989, 111, 9113. Angel, G.; Owczarczyk, Z.; Negishi, E. Tetrahedron Lett. 1992, 33, 1543.
    • (1992) Tetrahedron Lett. , vol.33 , pp. 1543
    • Angel, G.1    Owczarczyk, Z.2    Negishi, E.3
  • 16
    • 0001090887 scopus 로고
    • (c) Titanium: Grossman, R. B.; Buchwald, S. L. J. Org. Chem. 1992, 57, 5803. Berk, S. C.; Grosman, R. B.; Buchwald, S. L. J. Am. Chem. Soc. 1993, 115, 4912.
    • (1992) J. Org. Chem. , vol.57 , pp. 5803
    • Grossman, R.B.1    Buchwald, S.L.2
  • 20
    • 0000951442 scopus 로고
    • (e) Iron: Eaton, B. E.; Rollman, B.; Kaduk, J. A. J. Am. Chem. Soc. 1992, 114, 6245. Pearson, A. J.; Dubbert, R. A. Organometallics 1994, 13, 1656.
    • (1994) Organometallics , vol.13 , pp. 1656
    • Pearson, A.J.1    Dubbert, R.A.2
  • 24
    • 0010376317 scopus 로고
    • Pauson, P. L.; Khand, I. U. Ann. N. Y. Acad. Sci. 1977, 295, 2. Pauson, P. L. Tetrahedron 1985, 41, 5855. Pauson, P. L. In Organometallics in Organic Synthesis; de Meijere, A., tom Dieck, H., Eds.; Springer Verlag: Berlin, 1988; p 233-246. Shore, N. E. Chem. Rev. 1988, 88, 1085. Schore, N. E. Organic Reactions; John Wiley & Sons Inc.: New York, 1991; Vol. 40, p 1-90.
    • (1977) Ann. N. Y. Acad. Sci. , vol.295 , pp. 2
    • Pauson, P.L.1    Khand, I.U.2
  • 25
    • 0000134751 scopus 로고
    • Pauson, P. L.; Khand, I. U. Ann. N. Y. Acad. Sci. 1977, 295, 2. Pauson, P. L. Tetrahedron 1985, 41, 5855. Pauson, P. L. In Organometallics in Organic Synthesis; de Meijere, A., tom Dieck, H., Eds.; Springer Verlag: Berlin, 1988; p 233-246. Shore, N. E. Chem. Rev. 1988, 88, 1085. Schore, N. E. Organic Reactions; John Wiley & Sons Inc.: New York, 1991; Vol. 40, p 1-90.
    • (1985) Tetrahedron , vol.41 , pp. 5855
    • Pauson, P.L.1
  • 26
    • 0002804534 scopus 로고
    • de Meijere, A., tom Dieck, H., Eds.; Springer Verlag: Berlin
    • Pauson, P. L.; Khand, I. U. Ann. N. Y. Acad. Sci. 1977, 295, 2. Pauson, P. L. Tetrahedron 1985, 41, 5855. Pauson, P. L. In Organometallics in Organic Synthesis; de Meijere, A., tom Dieck, H., Eds.; Springer Verlag: Berlin, 1988; p 233-246. Shore, N. E. Chem. Rev. 1988, 88, 1085. Schore, N. E. Organic Reactions; John Wiley & Sons Inc.: New York, 1991; Vol. 40, p 1-90.
    • (1988) Organometallics in Organic Synthesis , pp. 233-246
    • Pauson, P.L.1
  • 27
    • 0013524753 scopus 로고
    • Pauson, P. L.; Khand, I. U. Ann. N. Y. Acad. Sci. 1977, 295, 2. Pauson, P. L. Tetrahedron 1985, 41, 5855. Pauson, P. L. In Organometallics in Organic Synthesis; de Meijere, A., tom Dieck, H., Eds.; Springer Verlag: Berlin, 1988; p 233-246. Shore, N. E. Chem. Rev. 1988, 88, 1085. Schore, N. E. Organic Reactions; John Wiley & Sons Inc.: New York, 1991; Vol. 40, p 1-90.
    • (1988) Chem. Rev. , vol.88 , pp. 1085
    • Shore, N.E.1
  • 28
    • 0002307453 scopus 로고
    • John Wiley & Sons Inc.: New York
    • Pauson, P. L.; Khand, I. U. Ann. N. Y. Acad. Sci. 1977, 295, 2. Pauson, P. L. Tetrahedron 1985, 41, 5855. Pauson, P. L. In Organometallics in Organic Synthesis; de Meijere, A., tom Dieck, H., Eds.; Springer Verlag: Berlin, 1988; p 233-246. Shore, N. E. Chem. Rev. 1988, 88, 1085. Schore, N. E. Organic Reactions; John Wiley & Sons Inc.: New York, 1991; Vol. 40, p 1-90.
    • (1991) Organic Reactions , vol.40 , pp. 1-90
    • Schore, N.E.1
  • 30
  • 32
    • 0025046680 scopus 로고
    • Smit, W. A.; Simonyan, S. O.; Tarasov, G. S. Mikaelian, G. S.; Gybin, A. S.; Ibaragimov, I. I. Caple, R.; Froen, O.; Kraeger, A. Synthesis 1989, 472. Shambayati, S.; Crowe, W. E.; Schreiber, S. L. Tetrahedron Lett. 1990, 31, 5289. Jeong, N.; Chung, Y. K.; Lee, B. Y.; Lee, S. H.; Yoo, S.-e. Synlett 1991, 204. Chung, Y. K.; Lee, B. Y.; Jeong, N.; Hudecek, M.; Pauson, P. L. Organometallics 1993, 12, 220.
    • (1990) Tetrahedron Lett. , vol.31 , pp. 5289
    • Shambayati, S.1    Crowe, W.E.2    Schreiber, S.L.3
  • 33
    • 85029867296 scopus 로고
    • Smit, W. A.; Simonyan, S. O.; Tarasov, G. S. Mikaelian, G. S.; Gybin, A. S.; Ibaragimov, I. I. Caple, R.; Froen, O.; Kraeger, A. Synthesis 1989, 472. Shambayati, S.; Crowe, W. E.; Schreiber, S. L. Tetrahedron Lett. 1990, 31, 5289. Jeong, N.; Chung, Y. K.; Lee, B. Y.; Lee, S. H.; Yoo, S.-e. Synlett 1991, 204. Chung, Y. K.; Lee, B. Y.; Jeong, N.; Hudecek, M.; Pauson, P. L. Organometallics 1993, 12, 220.
    • (1991) Synlett , pp. 204
    • Jeong, N.1    Chung, Y.K.2    Lee, B.Y.3    Lee, S.H.4    Yoo, S.-E.5
  • 34
    • 0000795340 scopus 로고
    • Smit, W. A.; Simonyan, S. O.; Tarasov, G. S. Mikaelian, G. S.; Gybin, A. S.; Ibaragimov, I. I. Caple, R.; Froen, O.; Kraeger, A. Synthesis 1989, 472. Shambayati, S.; Crowe, W. E.; Schreiber, S. L. Tetrahedron Lett. 1990, 31, 5289. Jeong, N.; Chung, Y. K.; Lee, B. Y.; Lee, S. H.; Yoo, S.-e. Synlett 1991, 204. Chung, Y. K.; Lee, B. Y.; Jeong, N.; Hudecek, M.; Pauson, P. L. Organometallics 1993, 12, 220.
    • (1993) Organometallics , vol.12 , pp. 220
    • Chung, Y.K.1    Lee, B.Y.2    Jeong, N.3    Hudecek, M.4    Pauson, P.L.5
  • 38
    • 0000115360 scopus 로고
    • Lautens, M.; Tam, W.; Sood, C. J. Org. Chem. 1993, 58, 4513. Lautens, M.; Tam, W., Lautens, J. C.; Edwards, L. G.; Crudden, C. M.; Smith, A. C. J. Am. Chem. Soc. 1995, 117, 6863.
    • (1993) J. Org. Chem. , vol.58 , pp. 4513
    • Lautens, M.1    Tam, W.2    Sood, C.3
  • 41
    • 85030191794 scopus 로고    scopus 로고
    • note
    • + calc. 276.1356, obsd. 276.1773.
  • 45
    • 85030186286 scopus 로고    scopus 로고
    • 4 the alkyne dicobalt hexacarbonyls react catalytically with strained alkenes under CO. Now a manuscript is in preparation
    • 4 the alkyne dicobalt hexacarbonyls react catalytically with strained alkenes under CO. Now a manuscript is in preparation.


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