메뉴 건너뛰기




Volumn 61, Issue 1, 1996, Pages 159-165

On the reaction of a dioxenylmolybdenum carbene complex with enynes: Studies of the intramolecular Diels-Alder reaction

Author keywords

[No Author keywords available]

Indexed keywords


EID: 0001706712     PISSN: 00223263     EISSN: None     Source Type: Journal    
DOI: 10.1021/jo9513370     Document Type: Article
Times cited : (20)

References (59)
  • 2
    • 0000048482 scopus 로고
    • Trost, B. M., Fleming, I., Eds.; Pergamon Press: Oxford
    • For reviews, see: (a) Roush, W. R. In Comprehensive Organic Synthesis; Trost, B. M., Fleming, I., Eds.; Pergamon Press: Oxford, 1991; Vol. 5, pp 513-550. (b) Fallis, A. G. Can. J. Chem. 1984, 62, 183-234. (c) Ciganek, E. Org. React. 1984, 32, 1-374.
    • (1991) Comprehensive Organic Synthesis , vol.5 , pp. 513-550
    • Roush, W.R.1
  • 3
    • 0003360065 scopus 로고
    • For reviews, see: (a) Roush, W. R. In Comprehensive Organic Synthesis; Trost, B. M., Fleming, I., Eds.; Pergamon Press: Oxford, 1991; Vol. 5, pp 513-550. (b) Fallis, A. G. Can. J. Chem. 1984, 62, 183-234. (c) Ciganek, E. Org. React. 1984, 32, 1-374.
    • (1984) Can. J. Chem. , vol.62 , pp. 183-234
    • Fallis, A.G.1
  • 4
    • 0003009874 scopus 로고
    • For reviews, see: (a) Roush, W. R. In Comprehensive Organic Synthesis; Trost, B. M., Fleming, I., Eds.; Pergamon Press: Oxford, 1991; Vol. 5, pp 513-550. (b) Fallis, A. G. Can. J. Chem. 1984, 62, 183-234. (c) Ciganek, E. Org. React. 1984, 32, 1-374.
    • (1984) Org. React. , vol.32 , pp. 1-374
    • Ciganek, E.1
  • 16
    • 5544235611 scopus 로고
    • Ph.D. dissertation, UCSD
    • Lund, K. P. Ph.D. dissertation, UCSD, 1992.
    • (1992)
    • Lund, K.P.1
  • 19
    • 0028095190 scopus 로고
    • and references cited therein
    • For a recent discussion of this effect, see: Parrill, A. L.; Dolata, D. P. Tetrahedron Lett. 1994, 35, 7319-7322 and references cited therein.
    • (1994) Tetrahedron Lett. , vol.35 , pp. 7319-7322
    • Parrill, A.L.1    Dolata, D.P.2
  • 21
    • 85033869418 scopus 로고    scopus 로고
    • Unpublished results
    • (b) Backenstrass, F. Unpublished results.
    • Backenstrass, F.1
  • 22
    • 0010589404 scopus 로고
    • For examples of metal-catalyzed [4 + 2] cycloadditions, see: (a) Carbonaro, A.; Greco, A.; Dall'Asta, G. J Org. Chem. 1968, 33, 3948-3950. (b) Genet, J. P.; Ficini, J. Tetrahedron Lett. 1979, 1499-1502. (c) Dieck, H. T.; Diercks, R. Angew. Chem., Int. Ed. Engl. 1983, 22, 778-779. (d) Mach, K.; Antropiusova, H.; Petrusova, L.; Turecek, F.; Hanus, V. J. Organomet. Chem. 1985, 289, 331-339. (e) Matsuda, I.; Shibata, M.; Sato, S.; Izumi, Y. Tetrahedron Lett. 1987, 28, 3361-3362. (f) Wender, P. A.; Jenkins, T. E. J. Am. Chem. Soc. 1989, 111, 6432-6434. (g) Jolly, R. S.; Luedtke, G.; Sheehan, D.; Livinghouse, T. J. Am. Chem. Soc. 1990, 112, 4965-4966. (h) Lautens, M ; Tam, W.; Edwards, L. G. J. Org. Chem. 1992, 57, 8-9. (i) McKinstry L.; Livinghouse, T. Tetrahedron 1994, 50, 6145-6154. (j) Wender, P. A.; Jenkins, T. E.; Suzuki, S. J. Am. Chem. Soc. 1995, 117, 1843-1844.
    • (1968) J Org. Chem. , vol.33 , pp. 3948-3950
    • Carbonaro, A.1    Greco, A.2    Dall'Asta, G.3
  • 23
    • 0002095620 scopus 로고
    • For examples of metal-catalyzed [4 + 2] cycloadditions, see: (a) Carbonaro, A.; Greco, A.; Dall'Asta, G. J Org. Chem. 1968, 33, 3948-3950. (b) Genet, J. P.; Ficini, J. Tetrahedron Lett. 1979, 1499-1502. (c) Dieck, H. T.; Diercks, R. Angew. Chem., Int. Ed. Engl. 1983, 22, 778-779. (d) Mach, K.; Antropiusova, H.; Petrusova, L.; Turecek, F.; Hanus, V. J. Organomet. Chem. 1985, 289, 331-339. (e) Matsuda, I.; Shibata, M.; Sato, S.; Izumi, Y. Tetrahedron Lett. 1987, 28, 3361-3362. (f) Wender, P. A.; Jenkins, T. E. J. Am. Chem. Soc. 1989, 111, 6432-6434. (g) Jolly, R. S.; Luedtke, G.; Sheehan, D.; Livinghouse, T. J. Am. Chem. Soc. 1990, 112, 4965-4966. (h) Lautens, M ; Tam, W.; Edwards, L. G. J. Org. Chem. 1992, 57, 8-9. (i) McKinstry L.; Livinghouse, T. Tetrahedron 1994, 50, 6145-6154. (j) Wender, P. A.; Jenkins, T. E.; Suzuki, S. J. Am. Chem. Soc. 1995, 117, 1843-1844.
    • (1979) Tetrahedron Lett. , pp. 1499-1502
    • Genet, J.P.1    Ficini, J.2
  • 24
    • 84940643310 scopus 로고
    • For examples of metal-catalyzed [4 + 2] cycloadditions, see: (a) Carbonaro, A.; Greco, A.; Dall'Asta, G. J Org. Chem. 1968, 33, 3948-3950. (b) Genet, J. P.; Ficini, J. Tetrahedron Lett. 1979, 1499-1502. (c) Dieck, H. T.; Diercks, R. Angew. Chem., Int. Ed. Engl. 1983, 22, 778-779. (d) Mach, K.; Antropiusova, H.; Petrusova, L.; Turecek, F.; Hanus, V. J. Organomet. Chem. 1985, 289, 331-339. (e) Matsuda, I.; Shibata, M.; Sato, S.; Izumi, Y. Tetrahedron Lett. 1987, 28, 3361-3362. (f) Wender, P. A.; Jenkins, T. E. J. Am. Chem. Soc. 1989, 111, 6432-6434. (g) Jolly, R. S.; Luedtke, G.; Sheehan, D.; Livinghouse, T. J. Am. Chem. Soc. 1990, 112, 4965-4966. (h) Lautens, M ; Tam, W.; Edwards, L. G. J. Org. Chem. 1992, 57, 8-9. (i) McKinstry L.; Livinghouse, T. Tetrahedron 1994, 50, 6145-6154. (j) Wender, P. A.; Jenkins, T. E.; Suzuki, S. J. Am. Chem. Soc. 1995, 117, 1843-1844.
    • (1983) Angew. Chem., Int. Ed. Engl. , vol.22 , pp. 778-779
    • Dieck, H.T.1    Diercks, R.2
  • 25
    • 0000730740 scopus 로고
    • For examples of metal-catalyzed [4 + 2] cycloadditions, see: (a) Carbonaro, A.; Greco, A.; Dall'Asta, G. J Org. Chem. 1968, 33, 3948-3950. (b) Genet, J. P.; Ficini, J. Tetrahedron Lett. 1979, 1499-1502. (c) Dieck, H. T.; Diercks, R. Angew. Chem., Int. Ed. Engl. 1983, 22, 778-779. (d) Mach, K.; Antropiusova, H.; Petrusova, L.; Turecek, F.; Hanus, V. J. Organomet. Chem. 1985, 289, 331-339. (e) Matsuda, I.; Shibata, M.; Sato, S.; Izumi, Y. Tetrahedron Lett. 1987, 28, 3361-3362. (f) Wender, P. A.; Jenkins, T. E. J. Am. Chem. Soc. 1989, 111, 6432-6434. (g) Jolly, R. S.; Luedtke, G.; Sheehan, D.; Livinghouse, T. J. Am. Chem. Soc. 1990, 112, 4965-4966. (h) Lautens, M ; Tam, W.; Edwards, L. G. J. Org. Chem. 1992, 57, 8-9. (i) McKinstry L.; Livinghouse, T. Tetrahedron 1994, 50, 6145-6154. (j) Wender, P. A.; Jenkins, T. E.; Suzuki, S. J. Am. Chem. Soc. 1995, 117, 1843-1844.
    • (1985) J. Organomet. Chem. , vol.289 , pp. 331-339
    • Mach, K.1    Antropiusova, H.2    Petrusova, L.3    Turecek, F.4    Hanus, V.5
  • 26
    • 0000514238 scopus 로고
    • For examples of metal-catalyzed [4 + 2] cycloadditions, see: (a) Carbonaro, A.; Greco, A.; Dall'Asta, G. J Org. Chem. 1968, 33, 3948-3950. (b) Genet, J. P.; Ficini, J. Tetrahedron Lett. 1979, 1499-1502. (c) Dieck, H. T.; Diercks, R. Angew. Chem., Int. Ed. Engl. 1983, 22, 778-779. (d) Mach, K.; Antropiusova, H.; Petrusova, L.; Turecek, F.; Hanus, V. J. Organomet. Chem. 1985, 289, 331-339. (e) Matsuda, I.; Shibata, M.; Sato, S.; Izumi, Y. Tetrahedron Lett. 1987, 28, 3361-3362. (f) Wender, P. A.; Jenkins, T. E. J. Am. Chem. Soc. 1989, 111, 6432-6434. (g) Jolly, R. S.; Luedtke, G.; Sheehan, D.; Livinghouse, T. J. Am. Chem. Soc. 1990, 112, 4965-4966. (h) Lautens, M ; Tam, W.; Edwards, L. G. J. Org. Chem. 1992, 57, 8-9. (i) McKinstry L.; Livinghouse, T. Tetrahedron 1994, 50, 6145-6154. (j) Wender, P. A.; Jenkins, T. E.; Suzuki, S. J. Am. Chem. Soc. 1995, 117, 1843-1844.
    • (1987) Tetrahedron Lett. , vol.28 , pp. 3361-3362
    • Matsuda, I.1    Shibata, M.2    Sato, S.3    Izumi, Y.4
  • 27
    • 33845185652 scopus 로고
    • For examples of metal-catalyzed [4 + 2] cycloadditions, see: (a) Carbonaro, A.; Greco, A.; Dall'Asta, G. J Org. Chem. 1968, 33, 3948-3950. (b) Genet, J. P.; Ficini, J. Tetrahedron Lett. 1979, 1499-1502. (c) Dieck, H. T.; Diercks, R. Angew. Chem., Int. Ed. Engl. 1983, 22, 778-779. (d) Mach, K.; Antropiusova, H.; Petrusova, L.; Turecek, F.; Hanus, V. J. Organomet. Chem. 1985, 289, 331-339. (e) Matsuda, I.; Shibata, M.; Sato, S.; Izumi, Y. Tetrahedron Lett. 1987, 28, 3361-3362. (f) Wender, P. A.; Jenkins, T. E. J. Am. Chem. Soc. 1989, 111, 6432-6434. (g) Jolly, R. S.; Luedtke, G.; Sheehan, D.; Livinghouse, T. J. Am. Chem. Soc. 1990, 112, 4965-4966. (h) Lautens, M ; Tam, W.; Edwards, L. G. J. Org. Chem. 1992, 57, 8-9. (i) McKinstry L.; Livinghouse, T. Tetrahedron 1994, 50, 6145-6154. (j) Wender, P. A.; Jenkins, T. E.; Suzuki, S. J. Am. Chem. Soc. 1995, 117, 1843-1844.
    • (1989) J. Am. Chem. Soc. , vol.111 , pp. 6432-6434
    • Wender, P.A.1    Jenkins, T.E.2
  • 28
    • 0001230097 scopus 로고
    • For examples of metal-catalyzed [4 + 2] cycloadditions, see: (a) Carbonaro, A.; Greco, A.; Dall'Asta, G. J Org. Chem. 1968, 33, 3948-3950. (b) Genet, J. P.; Ficini, J. Tetrahedron Lett. 1979, 1499-1502. (c) Dieck, H. T.; Diercks, R. Angew. Chem., Int. Ed. Engl. 1983, 22, 778-779. (d) Mach, K.; Antropiusova, H.; Petrusova, L.; Turecek, F.; Hanus, V. J. Organomet. Chem. 1985, 289, 331-339. (e) Matsuda, I.; Shibata, M.; Sato, S.; Izumi, Y. Tetrahedron Lett. 1987, 28, 3361-3362. (f) Wender, P. A.; Jenkins, T. E. J. Am. Chem. Soc. 1989, 111, 6432-6434. (g) Jolly, R. S.; Luedtke, G.; Sheehan, D.; Livinghouse, T. J. Am. Chem. Soc. 1990, 112, 4965-4966. (h) Lautens, M ; Tam, W.; Edwards, L. G. J. Org. Chem. 1992, 57, 8-9. (i) McKinstry L.; Livinghouse, T. Tetrahedron 1994, 50, 6145-6154. (j) Wender, P. A.; Jenkins, T. E.; Suzuki, S. J. Am. Chem. Soc. 1995, 117, 1843-1844.
    • (1990) J. Am. Chem. Soc. , vol.112 , pp. 4965-4966
    • Jolly, R.S.1    Luedtke, G.2    Sheehan, D.3    Livinghouse, T.4
  • 29
    • 33751391057 scopus 로고
    • For examples of metal-catalyzed [4 + 2] cycloadditions, see: (a) Carbonaro, A.; Greco, A.; Dall'Asta, G. J Org. Chem. 1968, 33, 3948-3950. (b) Genet, J. P.; Ficini, J. Tetrahedron Lett. 1979, 1499-1502. (c) Dieck, H. T.; Diercks, R. Angew. Chem., Int. Ed. Engl. 1983, 22, 778-779. (d) Mach, K.; Antropiusova, H.; Petrusova, L.; Turecek, F.; Hanus, V. J. Organomet. Chem. 1985, 289, 331-339. (e) Matsuda, I.; Shibata, M.; Sato, S.; Izumi, Y. Tetrahedron Lett. 1987, 28, 3361-3362. (f) Wender, P. A.; Jenkins, T. E. J. Am. Chem. Soc. 1989, 111, 6432-6434. (g) Jolly, R. S.; Luedtke, G.; Sheehan, D.; Livinghouse, T. J. Am. Chem. Soc. 1990, 112, 4965-4966. (h) Lautens, M ; Tam, W.; Edwards, L. G. J. Org. Chem. 1992, 57, 8-9. (i) McKinstry L.; Livinghouse, T. Tetrahedron 1994, 50, 6145-6154. (j) Wender, P. A.; Jenkins, T. E.; Suzuki, S. J. Am. Chem. Soc. 1995, 117, 1843-1844.
    • (1992) J. Org. Chem. , vol.57 , pp. 8-9
    • Lautens, M.1    Tam, W.2    Edwards, L.G.3
  • 30
    • 0028246445 scopus 로고
    • For examples of metal-catalyzed [4 + 2] cycloadditions, see: (a) Carbonaro, A.; Greco, A.; Dall'Asta, G. J Org. Chem. 1968, 33, 3948-3950. (b) Genet, J. P.; Ficini, J. Tetrahedron Lett. 1979, 1499-1502. (c) Dieck, H. T.; Diercks, R. Angew. Chem., Int. Ed. Engl. 1983, 22, 778-779. (d) Mach, K.; Antropiusova, H.; Petrusova, L.; Turecek, F.; Hanus, V. J. Organomet. Chem. 1985, 289, 331-339. (e) Matsuda, I.; Shibata, M.; Sato, S.; Izumi, Y. Tetrahedron Lett. 1987, 28, 3361-3362. (f) Wender, P. A.; Jenkins, T. E. J. Am. Chem. Soc. 1989, 111, 6432-6434. (g) Jolly, R. S.; Luedtke, G.; Sheehan, D.; Livinghouse, T. J. Am. Chem. Soc. 1990, 112, 4965-4966. (h) Lautens, M ; Tam, W.; Edwards, L. G. J. Org. Chem. 1992, 57, 8-9. (i) McKinstry L.; Livinghouse, T. Tetrahedron 1994, 50, 6145-6154. (j) Wender, P. A.; Jenkins, T. E.; Suzuki, S. J. Am. Chem. Soc. 1995, 117, 1843-1844.
    • (1994) Tetrahedron , vol.50 , pp. 6145-6154
    • McKinstry, L.1    Livinghouse, T.2
  • 31
    • 0000551283 scopus 로고
    • For examples of metal-catalyzed [4 + 2] cycloadditions, see: (a) Carbonaro, A.; Greco, A.; Dall'Asta, G. J Org. Chem. 1968, 33, 3948-3950. (b) Genet, J. P.; Ficini, J. Tetrahedron Lett. 1979, 1499-1502. (c) Dieck, H. T.; Diercks, R. Angew. Chem., Int. Ed. Engl. 1983, 22, 778-779. (d) Mach, K.; Antropiusova, H.; Petrusova, L.; Turecek, F.; Hanus, V. J. Organomet. Chem. 1985, 289, 331-339. (e) Matsuda, I.; Shibata, M.; Sato, S.; Izumi, Y. Tetrahedron Lett. 1987, 28, 3361-3362. (f) Wender, P. A.; Jenkins, T. E. J. Am. Chem. Soc. 1989, 111, 6432-6434. (g) Jolly, R. S.; Luedtke, G.; Sheehan, D.; Livinghouse, T. J. Am. Chem. Soc. 1990, 112, 4965-4966. (h) Lautens, M ; Tam, W.; Edwards, L. G. J. Org. Chem. 1992, 57, 8-9. (i) McKinstry L.; Livinghouse, T. Tetrahedron 1994, 50, 6145-6154. (j) Wender, P. A.; Jenkins, T. E.; Suzuki, S. J. Am. Chem. Soc. 1995, 117, 1843-1844.
    • (1995) J. Am. Chem. Soc. , vol.117 , pp. 1843-1844
    • Wender, P.A.1    Jenkins, T.E.2    Suzuki, S.3
  • 32
    • 33845278565 scopus 로고
    • For examples of other types of metal-promoted cycloaddition reactions, see: (a) Wender, P. A.; Ihle, N C.; Corriea, C. R. D. J. Am. Chem. Soc. 1988, 110, 5904-5906. (b) Chaffee, K.; Sheridan, J. B.; Aistars, A. Organometallics 1992, 11, 18-19. (c) Rigby, J. H. Acc. Chem. Res. 1993, 26, 579-585. (d) Kreiter, C. G.; Lehr, K. J. Organomet. Chem. 1993, 454, 199-207. (e) Wang, C.; Sheridan, J. B.; Chung, H.-J.; Cote, M. L.; Lalancette, R A.; Rheingold, A. L. J. Am. Chem. Soc. 1994, 116, 8966-8972.
    • (1988) J. Am. Chem. Soc. , vol.110 , pp. 5904-5906
    • Wender, P.A.1    Ihle, N.C.2    Corriea, C.R.D.3
  • 33
    • 0001866111 scopus 로고
    • For examples of other types of metal-promoted cycloaddition reactions, see: (a) Wender, P. A.; Ihle, N C.; Corriea, C. R. D. J. Am. Chem. Soc. 1988, 110, 5904-5906. (b) Chaffee, K.; Sheridan, J. B.; Aistars, A. Organometallics 1992, 11, 18-19. (c) Rigby, J. H. Acc. Chem. Res. 1993, 26, 579-585. (d) Kreiter, C. G.; Lehr, K. J. Organomet. Chem. 1993, 454, 199-207. (e) Wang, C.; Sheridan, J. B.; Chung, H.-J.; Cote, M. L.; Lalancette, R A.; Rheingold, A. L. J. Am. Chem. Soc. 1994, 116, 8966-8972.
    • (1992) Organometallics , vol.11 , pp. 18-19
    • Chaffee, K.1    Sheridan, J.B.2    Aistars, A.3
  • 34
    • 0000132340 scopus 로고
    • For examples of other types of metal-promoted cycloaddition reactions, see: (a) Wender, P. A.; Ihle, N C.; Corriea, C. R. D. J. Am. Chem. Soc. 1988, 110, 5904-5906. (b) Chaffee, K.; Sheridan, J. B.; Aistars, A. Organometallics 1992, 11, 18-19. (c) Rigby, J. H. Acc. Chem. Res. 1993, 26, 579-585. (d) Kreiter, C. G.; Lehr, K. J. Organomet. Chem. 1993, 454, 199-207. (e) Wang, C.; Sheridan, J. B.; Chung, H.-J.; Cote, M. L.; Lalancette, R A.; Rheingold, A. L. J. Am. Chem. Soc. 1994, 116, 8966-8972.
    • (1993) Acc. Chem. Res. , vol.26 , pp. 579-585
    • Rigby, J.H.1
  • 35
    • 43949163482 scopus 로고
    • For examples of other types of metal-promoted cycloaddition reactions, see: (a) Wender, P. A.; Ihle, N C.; Corriea, C. R. D. J. Am. Chem. Soc. 1988, 110, 5904-5906. (b) Chaffee, K.; Sheridan, J. B.; Aistars, A. Organometallics 1992, 11, 18-19. (c) Rigby, J. H. Acc. Chem. Res. 1993, 26, 579-585. (d) Kreiter, C. G.; Lehr, K. J. Organomet. Chem. 1993, 454, 199-207. (e) Wang, C.; Sheridan, J. B.; Chung, H.-J.; Cote, M. L.; Lalancette, R A.; Rheingold, A. L. J. Am. Chem. Soc. 1994, 116, 8966-8972.
    • (1993) J. Organomet. Chem. , vol.454 , pp. 199-207
    • Kreiter, C.G.1    Lehr, K.2
  • 36
    • 0038346111 scopus 로고
    • For examples of other types of metal-promoted cycloaddition reactions, see: (a) Wender, P. A.; Ihle, N C.; Corriea, C. R. D. J. Am. Chem. Soc. 1988, 110, 5904-5906. (b) Chaffee, K.; Sheridan, J. B.; Aistars, A. Organometallics 1992, 11, 18-19. (c) Rigby, J. H. Acc. Chem. Res. 1993, 26, 579-585. (d) Kreiter, C. G.; Lehr, K. J. Organomet. Chem. 1993, 454, 199-207. (e) Wang, C.; Sheridan, J. B.; Chung, H.-J.; Cote, M. L.; Lalancette, R A.; Rheingold, A. L. J. Am. Chem. Soc. 1994, 116, 8966-8972.
    • (1994) J. Am. Chem. Soc. , vol.116 , pp. 8966-8972
    • Wang, C.1    Sheridan, J.B.2    Chung, H.-J.3    Cote, M.L.4    Lalancette, R.A.5    Rheingold, A.L.6
  • 37
    • 0001281770 scopus 로고
    • and references therein
    • 1-complexes in iron-mediated triene cyclization reactions, see: Takacs, J. M.; Myoung, Y.-C.; Anderson, L. G. J. Org. Chem. 1994, 59, 6928-6942, and references therein.
    • (1994) J. Org. Chem. , vol.59 , pp. 6928-6942
    • Takacs, J.M.1    Myoung, Y.-C.2    Anderson, L.G.3
  • 38
    • 84970602196 scopus 로고
    • Wilkinson, G., Stone, F. G. A., Abel, E. W., Eds; Pergamon Press: Emsford, NY, and references cited therein
    • Davis, R.; Kane-Maguire, L. A. P. In Comprehensive Organometallic Chemistry; Wilkinson, G., Stone, F. G. A., Abel, E. W., Eds; Pergamon Press: Emsford, NY, 1982; Vol. 3, pp 1176-1203 and references cited therein.
    • (1982) Comprehensive Organometallic Chemistry , vol.3 , pp. 1176-1203
    • Davis, R.1    Kane-Maguire, L.A.P.2


* 이 정보는 Elsevier사의 SCOPUS DB에서 KISTI가 분석하여 추출한 것입니다.