Zr-catalyzed kinetic resolution of aliphatic cyclic allylic ethers. Carbocycles to heterocycles by Ru- and Mo-catalyzed ring-opening and ring- closing metathesis

Journal of Organic Chemistry

Volumn 64, Issue 26, 1999, Pages 9690-9696

  Adams, Jeffrey A ^a   Ford, J Gair ^a   Stamatos, Paul J ^a   Hoveyda, Amir H ^a  

^a BOSTON COLLEGE   (United States)

Author keywords

[No Author keywords available]

Indexed keywords

ALCOHOL; ALKENE; ETHER DERIVATIVE; FURAN DERIVATIVE; MOLYBDENUM; RUTHENIUM; ZIRCONIUM;

ARTICLE; CATALYSIS; CHEMICAL REACTION KINETICS; CHEMICAL STRUCTURE;

EID: 0033601296     PISSN: 00223263     EISSN: None     Source Type: Journal    
DOI: 10.1021/jo991323k     Document Type: Article

References (45)

1. (a) Harrity, J. P. A.; Visser, M. S.; Gleason, J. D.; Hoveyda, A. H. J. Am. Chem. Soc. 1997, 119, 1488-1489.
2. (b) Harrity, J. P. A.; La, D. S.; Cefalo, D. R.; Visser, M. S. J. Am. Chem. Soc. 1998, 120, 2343-2351.
3. (a) Morken, J. P.; Didiuk, M. T.; Hoveyda, A. H. J. Am. Chem. Soc. 1993, 115, 6697-6698.
4. (b) Didiuk, M. T.; Johannes, C. W.; Morken, J. P.; Hoveyda, A. H. J. Am. Chem. Soc. 1995, 117, 7097-7104.
5. (c) For a recent reviews, see: Hoveyda, A. H.; Morken, J. P. Angew. Chem., Int. Ed. Engl. 1996, 35, 1262-1284.
6. (d) Marek, I. J. Chem. Soc., Perkin Trans. 1 1999, 535-544.
7. For recent reviews of catalytic metathesis, see: (a) Grubbs, R. H.; Miller, S. J.; Fu, G. C. Acc. Chem. Res. 1995, 28, 446-452. (b) Schmalz, H.-G. Angew. Chem., Int. Ed. Engl. 1995, 107, 1833-1836. (c) Schuster, M.; Blechert, S. Angew. Chem., Int. Ed. Engl. 1997, 36, 2036-2056. (d) Armstrong, S. K. J. Chem. Soc., Perkin Trans. 1 1998, 371-388.
8. For recent reviews of catalytic metathesis, see: (a) Grubbs, R. H.; Miller, S. J.; Fu, G. C. Acc. Chem. Res. 1995, 28, 446-452. (b) Schmalz, H.-G. Angew. Chem., Int. Ed. Engl. 1995, 107, 1833-1836. (c) Schuster, M.; Blechert, S. Angew. Chem., Int. Ed. Engl. 1997, 36, 2036-2056. (d) Armstrong, S. K. J. Chem. Soc., Perkin Trans. 1 1998, 371-388.
9. For recent reviews of catalytic metathesis, see: (a) Grubbs, R. H.; Miller, S. J.; Fu, G. C. Acc. Chem. Res. 1995, 28, 446-452. (b) Schmalz, H.-G. Angew. Chem., Int. Ed. Engl. 1995, 107, 1833-1836. (c) Schuster, M.; Blechert, S. Angew. Chem., Int. Ed. Engl. 1997, 36, 2036-2056. (d) Armstrong, S. K. J. Chem. Soc., Perkin Trans. 1 1998, 371-388.
10. For recent reviews of catalytic metathesis, see: (a) Grubbs, R. H.; Miller, S. J.; Fu, G. C. Acc. Chem. Res. 1995, 28, 446-452. (b) Schmalz, H.-G. Angew. Chem., Int. Ed. Engl. 1995, 107, 1833-1836. (c) Schuster, M.; Blechert, S. Angew. Chem., Int. Ed. Engl. 1997, 36, 2036-2056. (d) Armstrong, S. K. J. Chem. Soc., Perkin Trans. 1 1998, 371-388.
11. Johannes, C. W.; Visser, M. S.; Weatherhead G. S.; Hoveyda, A. H. J. Am. Chem. Soc. 1998, 120, 8340-8347.
12. For a recent comprehensive review on metal-catalyzed kinetic resolution, see: Hoveyda, A. H.; Didiuk, M. T. Curr. Org. Chem. 1998, 2, 489-526.
13. Visser, M. S.; Hoveyda, A. H. Tetrahedron 1995, 51, 4383-4394.
14. (a) Morken, J. P.; Didiuk, M. T.; Visser, M. S.; Hoveyda, A. H. J. Am. Chem. Soc. 1994, 116, 3123-3124.
15. (b) Visser, M. S.; Heron, N. M.; Didiuk, M. T.; Sagal, J. F.; Hoveyda, A. H. J. Am. Chem. Soc. 1996, 118, 4291-4298.
16. Crowe, W. E.; Zhang, Z. J. J. Am. Chem. Soc. 1993, 115, 10998-10999.
17. Relative rates are calculated on the basis of the equation reported by Kagan. See: Kagan, H. B.; Fiaud, J. C. Top. Stereochem. 1988, 18, 249-330.
18. Visser, M. S.; Harrity, J. P. A.; Hoveyda, A. H. J. Am. Chem. Soc. 1996, 118, 3779-3780.
19. For an example of a catalytic reaction where a pendant acyclic π cloud directs the addition of the metal complex to a cyclic alkene to significantly facilitate the rate of the reaction, see: Trost, B. M.; Tasker, A. S.; Ruther, G.; Brandes, A. J. Am. Chem. Soc. 1991, 113, 670-672.
20. (a) Kitamura, M.; Kasahara, I.; Manabe, K.; Noyori, R.; Takaya, H. J. Org. Chem. 1988, 53, 708-710.
21. (b) Faller, J. W.; Tokunaga, M. Tetrahedron Lett. 1993, 34, 7359-7362.
22. (c) Corey, E. J.; Chen, C.-P.; Reichard, G. A. Tetrahedron Lett. 1989, 30, 5547-5550.
23. (d) Asami, M.; Suga, T.; Honda, K.; Inoue, S. Tetrahedron Lett. 1997, 36, 6425-6428.
24. (d) Gokhale, A. S.; Minidis, A. B. E.; Pfaltz, A. Tetrahedron Lett. 1995, 36, 1831-1834.
25. (e) Andrus, M. B.; Argade, A. B.; Chen, X.; Pamment, M. G. Tetrahedron Lett. 1995, 36, 2945-2948.
26. (f) Andrus, M. B.; Asgari, D.; Sclafani, J. A. J. Org. Chem. 1997, 62, 9365-9368.
27. (g) DattaGupta, A.; Singh, V. K. Tetrahedron Lett. 1996, 37, 2633-2636.
28. (h) Sodergren, M. J.; Andersson, P. G. Tetrahedron Lett. 1996, 37, 7577-7580.
29. (i) Kawasaki, K.; Katsuki, T. Tetrahedron 1997, 53, 6337-6350.
30. For Pd-catalyzed enantioselective synthesis of cyclic allylic esters, see: (j) Trost, B. M.; Organ, M. G. J. Am. Chem. Soc. 1994, 116, 10320-10321.
31. Schwab, P.; France, M. B.; Ziller, J. W.; Grubbs, R. H. Angew. Chem., Int. Ed. Engl. 1995, 34, 2039-2041.
32. For Mo-catalyzed ROM reactions, involving five-membered ring olefins, see: (a) Sita, L. R.; Lyon, S. R. J. Am. Chem. Soc. 1993, 115, 10374-10375. For related Ru-catalyzed ROM/RCM reactions, see: (b) Zuercher, W. J.; Hashimoto, M.; Grubbs, R. H. J. Am. Chem. Soc. 1996, 118, 6634-8640 and references therein. For representative recent reports on Ru-catalyzed ROM, see: (c) Snapper, M. L.; Tallarico, J. A.; Randall, M. L. J. Am. Chem. Soc. 1997, 119, 1478-1479. (d) Schneider, M. F.; Lucas, N.; Velder, J.; Blechert, S. Angew. Chem., Int. Ed. Engl. 1997, 36, 257-259.
33. For Mo-catalyzed ROM reactions, involving five-membered ring olefins, see: (a) Sita, L. R.; Lyon, S. R. J. Am. Chem. Soc. 1993, 115, 10374-10375. For related Ru-catalyzed ROM/RCM reactions, see: (b) Zuercher, W. J.; Hashimoto, M.; Grubbs, R. H. J. Am. Chem. Soc. 1996, 118, 6634-8640 and references therein. For representative recent reports on Ru-catalyzed ROM, see: (c) Snapper, M. L.; Tallarico, J. A.; Randall, M. L. J. Am. Chem. Soc. 1997, 119, 1478-1479. (d) Schneider, M. F.; Lucas, N.; Velder, J.; Blechert, S. Angew. Chem., Int. Ed. Engl. 1997, 36, 257-259.
34. For Mo-catalyzed ROM reactions, involving five-membered ring olefins, see: (a) Sita, L. R.; Lyon, S. R. J. Am. Chem. Soc. 1993, 115, 10374-10375. For related Ru-catalyzed ROM/RCM reactions, see: (b) Zuercher, W. J.; Hashimoto, M.; Grubbs, R. H. J. Am. Chem. Soc. 1996, 118, 6634-8640 and references therein. For representative recent reports on Ru-catalyzed ROM, see: (c) Snapper, M. L.; Tallarico, J. A.; Randall, M. L. J. Am. Chem. Soc. 1997, 119, 1478-1479. (d) Schneider, M. F.; Lucas, N.; Velder, J.; Blechert, S. Angew. Chem., Int. Ed. Engl. 1997, 36, 257-259.
35. For Mo-catalyzed ROM reactions, involving five-membered ring olefins, see: (a) Sita, L. R.; Lyon, S. R. J. Am. Chem. Soc. 1993, 115, 10374-10375. For related Ru-catalyzed ROM/RCM reactions, see: (b) Zuercher, W. J.; Hashimoto, M.; Grubbs, R. H. J. Am. Chem. Soc. 1996, 118, 6634-8640 and references therein. For representative recent reports on Ru-catalyzed ROM, see: (c) Snapper, M. L.; Tallarico, J. A.; Randall, M. L. J. Am. Chem. Soc. 1997, 119, 1478-1479. (d) Schneider, M. F.; Lucas, N.; Velder, J.; Blechert, S. Angew. Chem., Int. Ed. Engl. 1997, 36, 257-259.
36. The dimer we observe is the cross-metathesis product from reaction of the Ru-carbene (or Mo-alkylidene) derived from the terminal olefin of one product molecule with another product molecule through its terminal alkene. The example shown below is illustrative (dimer of 19). matrix presented "dimer" derived from 19
37. Calculations carried out at the BP/DN**//PM3 level indicate that whereas dihydrofurans derived from cyclopentenyl, cycloheptenyl, and cyclooctenyl ethers are thermodynamically lower in energy, products from cyclohexenyl substrates are higher in energy and the reaction is thus thermodynamically disfavored.
38. (a) Fox, H. H.; Yap, K. B.; Robbins, J.; Cai, S.; Schrock, R. R. Inorg. Chem. 1992, 31, 2287-2289.
39. (b) Schrock, R. R.; Murdzek, J. S.; Bazan, G. C.; Robbins, J.; DiMare, M.; O'Regan, M. J. Am. Chem. Soc. 1990, 112, 3875-3886.
40. (a) Alexander, J. B.; La, D. S.; Cefalo, D. R.; Hoveyda, A. H.; Schrock, R. R. J. Am. Chem. Soc. 1998, 120, 4041-4042.
41. (b) La, D. S.; Alexander, J. B.; Cefalo, D. R.; Graf, D. D.; Hoveyda, A. H.; Schrock, R. R. J. Am. Chem. Soc. 1998, 120, 9720-9721.
42. (c) Zhu, S.; Cefalo, D. R.; La, D. S.; Jamieson, J. Y.; Davis, W. M.; Hoveyda, A. H.; Schrock, R. R. J. Am. Chem. Soc. 1999, 121, 8251-8259.
43. (d) La, D. S.; Ford, J. G.; Sattely, E. S.; Bonitatebus, P. J.; Schrock, R. R.; Hoveyda, A. H. J. Am. Chem. Soc. 1999, 121, in press.
44. (a) Wild, F. R. W. P.; Waiucionek, M.; Huttner, G.; Brintzinger, H. H. J. Organomet. Chem. 1985, 288, 63-67.
45. (b) Diamond, G. M.; Rodewald, S.; Jordan, R. F. Organometallics 1995, 14, 5-7 and references therein.