Substituent effects on the Z/E-selectivity in cross-metathesis of conjugated enynes

Journal of Organic Chemistry

Volumn 69, Issue 22, 2004, Pages 7661-7664

  Kang, Byungman ^a   Lee, Ji Min ^a   Kwak, Jaesik ^a   Lee, Yoon Sup ^a   Chang, Sukbok ^a  

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

Author keywords

[No Author keywords available]

Indexed keywords

ISOMERS; SUBSTITUTION REACTIONS; SUBSTRATES;

CROSS-METATHESIS; SUBSTRATE MODIFICATION;

ORGANIC COMPOUNDS;

ALKENE DERIVATIVE; CYCLOBUTANE DERIVATIVE; ENYNE DERIVATIVE; LIGAND; METAL DERIVATIVE; POLYMER; RUTHENIUM; UNCLASSIFIED DRUG;

AB INITIO CALCULATION; ARTICLE; CATALYST; CHELATION; CHEMICAL INTERACTION; CHEMICAL MODEL; CHEMICAL MODIFICATION; CHEMICAL REACTION; CHEMICAL REACTION KINETICS; CHEMICAL STRUCTURE; CONJUGATE; CONTROL STRATEGY; CROSS METATHESIS; ISOMER; QUANTUM CHEMISTRY; REACTION ANALYSIS; STEREOCHEMISTRY; STEREOSPECIFICITY; SYNTHESIS; THERMODYNAMICS;

EID: 6344235270     PISSN: 00223263     EISSN: None     Source Type: Journal    
DOI: 10.1021/jo048883q     Document Type: Article

References (48)

1. For selected recent reviews, see: (a) Schuster, M.; Blechert, S. Angew. Chem., Int. Ed. Engl. 1997, 36, 2036.
2. (b) Grubbs, R. H.; Chang, S. Tetrahedron 1998, 54, 4413.
3. (c) Fürstner, A. Angew. Chem., Int. Ed. 2000, 39, 3012.
4. (d) Roy, R.; Das, S. K. Chem. Commun. 2000, 519.
5. (e) Trnka, T. M.; Grubbs, R. H. Acc. Chem. Res. 2001, 34, 18.
6. (f) Grubbs, R. H. Handbook of Olefin Metathesis; Wiley-VCH: Weinheim, Germany, 2003.
7. For recent representative reports on cross-metathesis, see: (a) Chatterjee, A. K.; Grubbs, R. H. Angew. Chem., Int. Ed. 2002, 41, 3171.
8. (b) Chatterjee, A. K.; Choi, T.-L.; Sanders, D. P.; Grubbs, R. H. J. Am. Chem. Soc. 2003, 125, 11360.
9. (c) Connon, S. J.; Blechert, S. Angew. Chem., Int. Ed. 2003, 42, 1900.
10. Chatterjee, A. K.; Choi, T.-L.; Sanders. D. P.; Grubbs, R. H. J. Am. Chem. Soc. 2003, 125, 11360.
11. (a) Jo, E.; Na, Y.; Chang, S. Tetrahedron Lett. 1999, 40, 5581.
12. (b) Lee, W.-W.; Chang, S. Tetrahedron: Asymmetry 1999, 10, 4473.
13. (c) Park, S.-H.; Kang, H. J.; Ko, S.; Park, S.; Chang, S. Tetrahedron: Asymmetry 2001, 12, 2621.
14. (d) Lee, W.-W.; Shin, H. J.; Chang, S. Tetrahedron: Asymmetry 2001, 12, 29.
15. (e) Chang, S.; Na, Y.; Shin, H. J.; Choi, E.; Jeong, L. S. Tetrahedron Lett. 2002, 43, 7445.
16. (f) Kang, B.; Chang, S. Tetrahedron 2004, 60, 7353.
17. Kang, B.; Kim, D.-h.; Do, Y.; Chang, S. Org. Lett. 2003, 5, 3041.
18. Although the detailed explanations were not presented, it was shown that CM of acrylonitrile afforded high Z-selectivity: Crowe, W. E.; Goldberg, D. R. J. Am. Chem. Soc. 1995, 117, 5162.
19. For a recent report on cross-metathesis of conjugated enynes and related mechanistic discussions, see: Hansen, E. C.; Lee, D. Org. Lett. 2004, 6, 2035.
20. For mechanistic studies of olefin metathesis, see: (a) Dias, E. L.; Nguyen, S. T.; Grubbs, R. H. J. Am. Chem. Soc. 1997, 119, 3887.
21. (b) Adlhart, C.; Hinderung, C.; Baumann, H.; Chen, P. J. Am. Chem. Soc. 2000, 122, 8204.
22. (c) Sanford, M. S.; Love, J. A.; Grubbs, R. H. J. Am. Chem. Soc. 2001, 123, 6543.
23. (d) Cavallo, L. J. Am. Chem. Soc. 2002, 124, 8965.
24. (e) Love, J. A.; Sanford, M. S.; Day, M. W.; Grubbs, R. H. J. Am. Chem. Soc. 2003, 125, 10103.
25. (f) Adlhart, C.; Chen, P. J. Am. Chem. Soc. 2004, 126, 3496.
26. (g) Seiders, T. J.; Ward, D. W.; Grubbs, R. H. Org. Lett. 2001, 3, 3225.
27. (h) Vyboishchikov, S. F.; Bühl, M.; Thiel, W. Chem. Eur. J. 2002, 8, 3962.
28. Love, J. A.; Morgan, J. P.; Trnka, T. M.; Grubbs, R. H. Angew. Chem., Int. Ed. 2002, 41, 4035.
29. The detailed experiment procedure is available in Supporting Information.
30. Hérrisson, J. L.; Chauvin, Y. Makromol. Chem. 1970, 141, 161.
31. For a previous example of kinetically controlled CM leading to preferential formation of E-olefins, see: Engelhardt, F. C.; Schmitt, M. J.; Taylor, R. E. Org. Lett. 2001, 3, 2209.
32. Conjugated enynes were readily prepared by the reaction of vinyl or propenyl bromide with the corresponding alkynes under the Sonogashira conditions.
33. For an analogous explanation of observed stereochemistry in polymerization metathesis, see: Krause, J. O.; Zarka, M. T.; Anders, U.; Weberskirch, R.; Nuyken, O.; Buchmeiser, M. R. Angew. Chem., Int. Ed. 2003, 42, 5965.
34. For previous examples involving chelation-based metathesis structures, see: (a) Fürstner, A.; Langemann, K. J. Am. Chem. Soc. 1997, 119, 9130.
35. (b) Ghosh, A. K.; Cappiello, J.; Shin, D. Tetrahedron Lett. 1998, 39, 4651.
36. (c) Kingsbury, J. S.; Harrity, J. P. A.; Bonitatebus, P. J., Jr.; Hoveyda, A. H. J. Am. Chem. Soc. 1999, 121, 791.
37. (d) Choi, T.-L.; Chatterjee, A. K.; Grubbs, R. H. Angew. Chem., Int. Ed. 2001, 40, 1277.
38. (e) Courchay, F. C.; Sworen, J. C.; Wagener, K. B. Macromolecules 2003, 36, 8231.
39. For the mechanistic studies of olefin metathesis using quantum molecular dynamics, see: (a) Aagaard, O. M.; Meier, R. J.; Buda, F. J. Am. Chem. Soc. 1998, 120, 7174.
40. (b) Hansen, S. M.; Rominger, F.; Metz, M.; Hofmann, P. Chem. Eur. J. 1999, 5, 557.
41. (c) Suresh, C. H.; Koga, N. Organometallics 2004, 23, 76.
42. Ivanciuc, O. J. Chem. Inf. Comput. Sci. 1996, 36, 612.
43. Frisch, M. J.; Pople, J. A.; Binkley, J. S. J. Chem. Phys. 1984, 80, 3265.
44. (a) Hohenberg, P.; Kohn, W. Phys. Rev. 1964, 136, 864.
45. (b) Pople, J. A.; Gil, P. M. W.; Johnson, B. G. Chem. Phys. Lett. 1992, 199, 557.
46. Sosa, C.; Andzelm, J.; Elkin, B. C.; Wimmer, E.; Dobbs, K. D.; Dixon, D. A. J. Phys. Chem. 1992, 96, 6630.
47. Detailed values of the calculation performed in this study are presented in Supporting Information.
48. For the reference of the energy values, see: Dobbs, K. D.; Hehre, W. J. J. Comput. Chem. 1987, 8, 861.