Conjugated enynes as a new type of substrates for olefin metathesis

Organic Letters

Volumn 5, Issue 17, 2003, Pages 3041-3043

  Kang, Byungman ^a   Kim, Do Hyeon ^a   Do, Youngkyu ^a   Chang, Sukbok ^a  

^a Korea Advanced Institute of Science and Technology (KAIST)   (South Korea)

Author keywords

[No Author keywords available]

Indexed keywords

ALKENE; BENZYL DERIVATIVE; CYCLOALKENE; PYRIDINE DERIVATIVE; RUTHENIUM DERIVATIVE;

ARTICLE; CATALYST; CONJUGATION; ISOMER; RING CLOSING METATHESIS; SYNTHESIS;

EID: 0141520697     PISSN: 15237060     EISSN: None     Source Type: Journal    
DOI: 10.1021/ol035014z     Document Type: Article

References (30)

1. For recent reviews of olefin metathesis, see: (a) Schuster, M.; Blechert, S. Angew. Chem., Int. Ed. 1997, 36, 2037. (b) Grubbs, R. H.; Chang, S. Tetrahedron 1998, 54, 4413. (c) Fürstner, A. Angew. Chem., Int. Ed. 2000, 39, 3012. (d) Trnka, T. M.; Grubbs, R. H. Acc. Chem. Res. 2001, 34, 18. (e) Connon, S. J.; Blechert, S. Angew. Chem., Int. Ed. 2003, 42, 1900.
2. For recent reviews of olefin metathesis, see: (a) Schuster, M.; Blechert, S. Angew. Chem., Int. Ed. 1997, 36, 2037. (b) Grubbs, R. H.; Chang, S. Tetrahedron 1998, 54, 4413. (c) Fürstner, A. Angew. Chem., Int. Ed. 2000, 39, 3012. (d) Trnka, T. M.; Grubbs, R. H. Acc. Chem. Res. 2001, 34, 18. (e) Connon, S. J.; Blechert, S. Angew. Chem., Int. Ed. 2003, 42, 1900.
3. For recent reviews of olefin metathesis, see: (a) Schuster, M.; Blechert, S. Angew. Chem., Int. Ed. 1997, 36, 2037. (b) Grubbs, R. H.; Chang, S. Tetrahedron 1998, 54, 4413. (c) Fürstner, A. Angew. Chem., Int. Ed. 2000, 39, 3012. (d) Trnka, T. M.; Grubbs, R. H. Acc. Chem. Res. 2001, 34, 18. (e) Connon, S. J.; Blechert, S. Angew. Chem., Int. Ed. 2003, 42, 1900.
4. For recent reviews of olefin metathesis, see: (a) Schuster, M.; Blechert, S. Angew. Chem., Int. Ed. 1997, 36, 2037. (b) Grubbs, R. H.; Chang, S. Tetrahedron 1998, 54, 4413. (c) Fürstner, A. Angew. Chem., Int. Ed. 2000, 39, 3012. (d) Trnka, T. M.; Grubbs, R. H. Acc. Chem. Res. 2001, 34, 18. (e) Connon, S. J.; Blechert, S. Angew. Chem., Int. Ed. 2003, 42, 1900.
5. For recent reviews of olefin metathesis, see: (a) Schuster, M.; Blechert, S. Angew. Chem., Int. Ed. 1997, 36, 2037. (b) Grubbs, R. H.; Chang, S. Tetrahedron 1998, 54, 4413. (c) Fürstner, A. Angew. Chem., Int. Ed. 2000, 39, 3012. (d) Trnka, T. M.; Grubbs, R. H. Acc. Chem. Res. 2001, 34, 18. (e) Connon, S. J.; Blechert, S. Angew. Chem., Int. Ed. 2003, 42, 1900.
6. For selected examples, see: (a) Ashe, A. J., III; Fang, X. Org. Lett. 2000, 2, 2089. (b) Williams, D. R.; Cortez, G. S.; Bogen, S. L.; Rojas, C. M. Angew. Chem., Int. Ed. 2000, 39, 4612. (c) Garbaccio, R. M.; Stachel, S. J.; Baeschlin, D. K.; Danishefsky, S. J. J. Am. Chem. Soc. 2001, 123, 10903.
7. For selected examples, see: (a) Ashe, A. J., III; Fang, X. Org. Lett. 2000, 2, 2089. (b) Williams, D. R.; Cortez, G. S.; Bogen, S. L.; Rojas, C. M. Angew. Chem., Int. Ed. 2000, 39, 4612. (c) Garbaccio, R. M.; Stachel, S. J.; Baeschlin, D. K.; Danishefsky, S. J. J. Am. Chem. Soc. 2001, 123, 10903.
8. For selected examples, see: (a) Ashe, A. J., III; Fang, X. Org. Lett. 2000, 2, 2089. (b) Williams, D. R.; Cortez, G. S.; Bogen, S. L.; Rojas, C. M. Angew. Chem., Int. Ed. 2000, 39, 4612. (c) Garbaccio, R. M.; Stachel, S. J.; Baeschlin, D. K.; Danishefsky, S. J. J. Am. Chem. Soc. 2001, 123, 10903.
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17. Observation that the original triple-bond stretching frequency of 4 disappeared almost completely upon addition of 0.5 equiv of 2 might indicate that two alkynes coordinate to the ruthenium center.
18. 2, the original carbene peak (18.99 ppm) disappeared gradually on NMR and only a new peak (18.29 ppm, singlet) was observed after 2 h at 40 °C.
19. Love, J. A.; Morgan, J. P.; Trnka, T. M.; Grubbs, R. H. Angew. Chem., Int. Ed. 2002, 41, 4035.
20. Bispyridine-substituted ruthenium carbene complex 3 was prepared according to a literature procedure (ref 10) with 80-85% yields.
21. Recently, kinetically controlled cross-metathesis of alkenes with high (E)-selectivity has been reported, see: Engelhardt, F. C.; Schmitt, M. J.; Taylor, R. E. Org. Lett. 2001, 3, 2209.
22. Lee and Grubbs have described the effects of positioning an auxiliary group onto the terminal olefinic site on the stereochemistry of ring formation; see: Lee, C. W.; Grubbs, R. H. Org. Lett. 2000, 2, 2145.
23. Previously, acrylonitrile was found to undergo cross-metathesis with high cis-selectivity; see: Crowe, W. E.; Goldberg, D. R. J. Am. Chem. Soc. 1995, 117, 5162.
24. Conjugated enynes were prepared in high yields from alkynes with vinyl bromides using Sonogashira conditions. See Supporting Information.
25. For previous studies of ethylene effects on enyne metathesis, see: (a) Mori, M.; Sakakibara, N.; Kinoshita, A. J. Org. Chem. 1998, 63, 6082. (b) Smulik, J. A.; Diver, S. T. J. Org. Chem. 2000, 65, 1788.
26. For previous studies of ethylene effects on enyne metathesis, see: (a) Mori, M.; Sakakibara, N.; Kinoshita, A. J. Org. Chem. 1998, 63, 6082. (b) Smulik, J. A.; Diver, S. T. J. Org. Chem. 2000, 65, 1788.
27. (a) Couturier, M.; Brassard, P. Synthesis 1994, 703.
28. (b) Jenneskens, L. W.; de Wolf, W. H.; Bickelhaupt, F. Chem. Ber. 1986, 119, 754.
29. Cycloaddition reactions proceeded smoothly and quantitatively also for other cyclic trienes prepared in this study.
30. Detailed X-ray analysis data of compound 15 are described in Supporting Information.