Tandem radical reactions and ring-closing metathesis. Application in the synthesis of cyclooctenes

Organic Letters

Volumn 5, Issue 16, 2003, Pages 2883-2886

  Sibi, Mukund P ^a   Aasmul, Mona ^a   Hasegawa, Hikaru ^a   Subramanian, Thangaiah ^a  

^a NORTH DAKOTA STATE UNIVERSITY   (United States)

Author keywords

[No Author keywords available]

Indexed keywords

ALKADIENE; ALKENE DERIVATIVE;

ARTICLE; CATALYSIS; CATALYST; CHEMICAL REACTION; RADICAL REACTION; RING CLOSING METATHESIS;

ALKENES; FREE RADICALS;

EID: 0141520531     PISSN: 15237060     EISSN: None     Source Type: Journal    
DOI: 10.1021/ol034924d     Document Type: Article

References (42)

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6. For recent reviews on ring-closing metathesis, see: (a) Trnka, T. M.; Grubbs, R. H. Acc. Chem. Res. 2001, 34, 18. (b) Fürstner, A. Angew. Chem., Int. Ed. 2000, 39, 3012.
7. For recent reviews on ring-closing metathesis, see: (a) Trnka, T. M.; Grubbs, R. H. Acc. Chem. Res. 2001, 34, 18. (b) Fürstner, A. Angew. Chem., Int. Ed. 2000, 39, 3012.
8. For selected reports on the formation five-membered rings using RCM, see: (a) Mayo, K. G.; Nearhoof, E. H.; Kiddle, J. J. Org. Lett. 2002, 4, 1567. (b) Oesterreich, K.; Spitzner, D. Tetrahedron 2002, 58, 4331. (c) Seiders, T. J.; Ward, D. W.; Grubbs, R. H. Org. Lett. 2001, 3, 3225. (d) Briot, A.; Bujard, M.; Gouverneur, V.; Nolan, S. P.; Mioskowski, C. Org. Lett. 2000, 2, 1517. (e) Scholl, M.; Ding, S.; Lee, C. W.; Grubbs, R. H. Org. Lett. 1999, 1, 953. For six-membered rings, see: (f) Abell, A. D.; Gardiner, J. Org. Lett. 2002, 4, 3663. (g) Reddy, Y. K.; Falck, J. R. Org. Lett. 2002, 4, 969. (h) Ma, S.; Ni, B. Org. Lett. 2002, 4, 639. (i) Ghosh, A. K.; Wang, Y.; Kim, J. T. J. Org. Chem. 2001, 66, 8973.
9. For selected reports on the formation five-membered rings using RCM, see: (a) Mayo, K. G.; Nearhoof, E. H.; Kiddle, J. J. Org. Lett. 2002, 4, 1567. (b) Oesterreich, K.; Spitzner, D. Tetrahedron 2002, 58, 4331. (c) Seiders, T. J.; Ward, D. W.; Grubbs, R. H. Org. Lett. 2001, 3, 3225. (d) Briot, A.; Bujard, M.; Gouverneur, V.; Nolan, S. P.; Mioskowski, C. Org. Lett. 2000, 2, 1517. (e) Scholl, M.; Ding, S.; Lee, C. W.; Grubbs, R. H. Org. Lett. 1999, 1, 953. For six-membered rings, see: (f) Abell, A. D.; Gardiner, J. Org. Lett. 2002, 4, 3663. (g) Reddy, Y. K.; Falck, J. R. Org. Lett. 2002, 4, 969. (h) Ma, S.; Ni, B. Org. Lett. 2002, 4, 639. (i) Ghosh, A. K.; Wang, Y.; Kim, J. T. J. Org. Chem. 2001, 66, 8973.
10. For selected reports on the formation five-membered rings using RCM, see: (a) Mayo, K. G.; Nearhoof, E. H.; Kiddle, J. J. Org. Lett. 2002, 4, 1567. (b) Oesterreich, K.; Spitzner, D. Tetrahedron 2002, 58, 4331. (c) Seiders, T. J.; Ward, D. W.; Grubbs, R. H. Org. Lett. 2001, 3, 3225. (d) Briot, A.; Bujard, M.; Gouverneur, V.; Nolan, S. P.; Mioskowski, C. Org. Lett. 2000, 2, 1517. (e) Scholl, M.; Ding, S.; Lee, C. W.; Grubbs, R. H. Org. Lett. 1999, 1, 953. For six-membered rings, see: (f) Abell, A. D.; Gardiner, J. Org. Lett. 2002, 4, 3663. (g) Reddy, Y. K.; Falck, J. R. Org. Lett. 2002, 4, 969. (h) Ma, S.; Ni, B. Org. Lett. 2002, 4, 639. (i) Ghosh, A. K.; Wang, Y.; Kim, J. T. J. Org. Chem. 2001, 66, 8973.
11. For selected reports on the formation five-membered rings using RCM, see: (a) Mayo, K. G.; Nearhoof, E. H.; Kiddle, J. J. Org. Lett. 2002, 4, 1567. (b) Oesterreich, K.; Spitzner, D. Tetrahedron 2002, 58, 4331. (c) Seiders, T. J.; Ward, D. W.; Grubbs, R. H. Org. Lett. 2001, 3, 3225. (d) Briot, A.; Bujard, M.; Gouverneur, V.; Nolan, S. P.; Mioskowski, C. Org. Lett. 2000, 2, 1517. (e) Scholl, M.; Ding, S.; Lee, C. W.; Grubbs, R. H. Org. Lett. 1999, 1, 953. For six-membered rings, see: (f) Abell, A. D.; Gardiner, J. Org. Lett. 2002, 4, 3663. (g) Reddy, Y. K.; Falck, J. R. Org. Lett. 2002, 4, 969. (h) Ma, S.; Ni, B. Org. Lett. 2002, 4, 639. (i) Ghosh, A. K.; Wang, Y.; Kim, J. T. J. Org. Chem. 2001, 66, 8973.
12. For selected reports on the formation five-membered rings using RCM, see: (a) Mayo, K. G.; Nearhoof, E. H.; Kiddle, J. J. Org. Lett. 2002, 4, 1567. (b) Oesterreich, K.; Spitzner, D. Tetrahedron 2002, 58, 4331. (c) Seiders, T. J.; Ward, D. W.; Grubbs, R. H. Org. Lett. 2001, 3, 3225. (d) Briot, A.; Bujard, M.; Gouverneur, V.; Nolan, S. P.; Mioskowski, C. Org. Lett. 2000, 2, 1517. (e) Scholl, M.; Ding, S.; Lee, C. W.; Grubbs, R. H. Org. Lett. 1999, 1, 953. For six-membered rings, see: (f) Abell, A. D.; Gardiner, J. Org. Lett. 2002, 4, 3663. (g) Reddy, Y. K.; Falck, J. R. Org. Lett. 2002, 4, 969. (h) Ma, S.; Ni, B. Org. Lett. 2002, 4, 639. (i) Ghosh, A. K.; Wang, Y.; Kim, J. T. J. Org. Chem. 2001, 66, 8973.
13. For selected reports on the formation five-membered rings using RCM, see: (a) Mayo, K. G.; Nearhoof, E. H.; Kiddle, J. J. Org. Lett. 2002, 4, 1567. (b) Oesterreich, K.; Spitzner, D. Tetrahedron 2002, 58, 4331. (c) Seiders, T. J.; Ward, D. W.; Grubbs, R. H. Org. Lett. 2001, 3, 3225. (d) Briot, A.; Bujard, M.; Gouverneur, V.; Nolan, S. P.; Mioskowski, C. Org. Lett. 2000, 2, 1517. (e) Scholl, M.; Ding, S.; Lee, C. W.; Grubbs, R. H. Org. Lett. 1999, 1, 953. For six-membered rings, see: (f) Abell, A. D.; Gardiner, J. Org. Lett. 2002, 4, 3663. (g) Reddy, Y. K.; Falck, J. R. Org. Lett. 2002, 4, 969. (h) Ma, S.; Ni, B. Org. Lett. 2002, 4, 639. (i) Ghosh, A. K.; Wang, Y.; Kim, J. T. J. Org. Chem. 2001, 66, 8973.
14. For selected reports on the formation five-membered rings using RCM, see: (a) Mayo, K. G.; Nearhoof, E. H.; Kiddle, J. J. Org. Lett. 2002, 4, 1567. (b) Oesterreich, K.; Spitzner, D. Tetrahedron 2002, 58, 4331. (c) Seiders, T. J.; Ward, D. W.; Grubbs, R. H. Org. Lett. 2001, 3, 3225. (d) Briot, A.; Bujard, M.; Gouverneur, V.; Nolan, S. P.; Mioskowski, C. Org. Lett. 2000, 2, 1517. (e) Scholl, M.; Ding, S.; Lee, C. W.; Grubbs, R. H. Org. Lett. 1999, 1, 953. For six-membered rings, see: (f) Abell, A. D.; Gardiner, J. Org. Lett. 2002, 4, 3663. (g) Reddy, Y. K.; Falck, J. R. Org. Lett. 2002, 4, 969. (h) Ma, S.; Ni, B. Org. Lett. 2002, 4, 639. (i) Ghosh, A. K.; Wang, Y.; Kim, J. T. J. Org. Chem. 2001, 66, 8973.
15. For selected reports on the formation five-membered rings using RCM, see: (a) Mayo, K. G.; Nearhoof, E. H.; Kiddle, J. J. Org. Lett. 2002, 4, 1567. (b) Oesterreich, K.; Spitzner, D. Tetrahedron 2002, 58, 4331. (c) Seiders, T. J.; Ward, D. W.; Grubbs, R. H. Org. Lett. 2001, 3, 3225. (d) Briot, A.; Bujard, M.; Gouverneur, V.; Nolan, S. P.; Mioskowski, C. Org. Lett. 2000, 2, 1517. (e) Scholl, M.; Ding, S.; Lee, C. W.; Grubbs, R. H. Org. Lett. 1999, 1, 953. For six-membered rings, see: (f) Abell, A. D.; Gardiner, J. Org. Lett. 2002, 4, 3663. (g) Reddy, Y. K.; Falck, J. R. Org. Lett. 2002, 4, 969. (h) Ma, S.; Ni, B. Org. Lett. 2002, 4, 639. (i) Ghosh, A. K.; Wang, Y.; Kim, J. T. J. Org. Chem. 2001, 66, 8973.
16. For selected reports on the formation five-membered rings using RCM, see: (a) Mayo, K. G.; Nearhoof, E. H.; Kiddle, J. J. Org. Lett. 2002, 4, 1567. (b) Oesterreich, K.; Spitzner, D. Tetrahedron 2002, 58, 4331. (c) Seiders, T. J.; Ward, D. W.; Grubbs, R. H. Org. Lett. 2001, 3, 3225. (d) Briot, A.; Bujard, M.; Gouverneur, V.; Nolan, S. P.; Mioskowski, C. Org. Lett. 2000, 2, 1517. (e) Scholl, M.; Ding, S.; Lee, C. W.; Grubbs, R. H. Org. Lett. 1999, 1, 953. For six-membered rings, see: (f) Abell, A. D.; Gardiner, J. Org. Lett. 2002, 4, 3663. (g) Reddy, Y. K.; Falck, J. R. Org. Lett. 2002, 4, 969. (h) Ma, S.; Ni, B. Org. Lett. 2002, 4, 639. (i) Ghosh, A. K.; Wang, Y.; Kim, J. T. J. Org. Chem. 2001, 66, 8973.
17. For recent papers on eight-membered ring synthesis, see: (a) Bourgeois, D.; Pancrazi, A.; Nolan, S. P.; Prunet, J. J. Organomet. Chem. 2002, 643-644, 247. (b) Ruprah, P. K.; Cros, J.-P.; Pease, J. E.; Whittingham, W. G.; Williams, J. M. J. Eur. J. Org. Chem. 2002, 3145. (c) Kariuki, B. M.; Owton, W. M.; Percy, J. M.; Pintat, S.; Smith, C. A.; Spencer, N. S.; Thomas, A. C.; Watson, M. Chem. Commun. 2002, 228. (d) Boyer, F.-D.; Hanna, I.; Nolan, S. P. J. Org. Chem. 2001, 66, 4094. (e) Hanna, I.; Ricard, L. Org. Lett. 2000, 2, 2651. (f) Bourgeois, D.; Pancrazi, A.; Ricard, L.; Prunet, J. Angew. Chem., Int. Ed. 2000, 39, 725. (g) Bieräugel, H.; Jansen, T. P.; Schoemaker, H. E.; Hiemstra, H.; van Maarseveen, J. H. Org. Lett. 2002, 4, 2673. (h) Fürstner, A.; Thiel, O. R.; Ackermann, L.; Schanz, H.-J.; Nolan, S. P. J. Org. Chem. 2000, 65, 2204. (i) Buijsman, R. C.; van Vuuren, E.; Sterrenburg, J. G. Org. Lett. 2001, 3, 3785. (j) Tarling, C. A.; Holmes, A. B.; Marwell, R. E. Pearson, N. D. J. Chem. Soc., Perkin Trans. 1 1999, 1695.
18. For recent papers on eight-membered ring synthesis, see: (a) Bourgeois, D.; Pancrazi, A.; Nolan, S. P.; Prunet, J. J. Organomet. Chem. 2002, 643-644, 247. (b) Ruprah, P. K.; Cros, J.-P.; Pease, J. E.; Whittingham, W. G.; Williams, J. M. J. Eur. J. Org. Chem. 2002, 3145. (c) Kariuki, B. M.; Owton, W. M.; Percy, J. M.; Pintat, S.; Smith, C. A.; Spencer, N. S.; Thomas, A. C.; Watson, M. Chem. Commun. 2002, 228. (d) Boyer, F.-D.; Hanna, I.; Nolan, S. P. J. Org. Chem. 2001, 66, 4094. (e) Hanna, I.; Ricard, L. Org. Lett. 2000, 2, 2651. (f) Bourgeois, D.; Pancrazi, A.; Ricard, L.; Prunet, J. Angew. Chem., Int. Ed. 2000, 39, 725. (g) Bieräugel, H.; Jansen, T. P.; Schoemaker, H. E.; Hiemstra, H.; van Maarseveen, J. H. Org. Lett. 2002, 4, 2673. (h) Fürstner, A.; Thiel, O. R.; Ackermann, L.; Schanz, H.-J.; Nolan, S. P. J. Org. Chem. 2000, 65, 2204. (i) Buijsman, R. C.; van Vuuren, E.; Sterrenburg, J. G. Org. Lett. 2001, 3, 3785. (j) Tarling, C. A.; Holmes, A. B.; Marwell, R. E. Pearson, N. D. J. Chem. Soc., Perkin Trans. 1 1999, 1695.
19. For recent papers on eight-membered ring synthesis, see: (a) Bourgeois, D.; Pancrazi, A.; Nolan, S. P.; Prunet, J. J. Organomet. Chem. 2002, 643-644, 247. (b) Ruprah, P. K.; Cros, J.-P.; Pease, J. E.; Whittingham, W. G.; Williams, J. M. J. Eur. J. Org. Chem. 2002, 3145. (c) Kariuki, B. M.; Owton, W. M.; Percy, J. M.; Pintat, S.; Smith, C. A.; Spencer, N. S.; Thomas, A. C.; Watson, M. Chem. Commun. 2002, 228. (d) Boyer, F.-D.; Hanna, I.; Nolan, S. P. J. Org. Chem. 2001, 66, 4094. (e) Hanna, I.; Ricard, L. Org. Lett. 2000, 2, 2651. (f) Bourgeois, D.; Pancrazi, A.; Ricard, L.; Prunet, J. Angew. Chem., Int. Ed. 2000, 39, 725. (g) Bieräugel, H.; Jansen, T. P.; Schoemaker, H. E.; Hiemstra, H.; van Maarseveen, J. H. Org. Lett. 2002, 4, 2673. (h) Fürstner, A.; Thiel, O. R.; Ackermann, L.; Schanz, H.-J.; Nolan, S. P. J. Org. Chem. 2000, 65, 2204. (i) Buijsman, R. C.; van Vuuren, E.; Sterrenburg, J. G. Org. Lett. 2001, 3, 3785. (j) Tarling, C. A.; Holmes, A. B.; Marwell, R. E. Pearson, N. D. J. Chem. Soc., Perkin Trans. 1 1999, 1695.
20. For recent papers on eight-membered ring synthesis, see: (a) Bourgeois, D.; Pancrazi, A.; Nolan, S. P.; Prunet, J. J. Organomet. Chem. 2002, 643-644, 247. (b) Ruprah, P. K.; Cros, J.-P.; Pease, J. E.; Whittingham, W. G.; Williams, J. M. J. Eur. J. Org. Chem. 2002, 3145. (c) Kariuki, B. M.; Owton, W. M.; Percy, J. M.; Pintat, S.; Smith, C. A.; Spencer, N. S.; Thomas, A. C.; Watson, M. Chem. Commun. 2002, 228. (d) Boyer, F.-D.; Hanna, I.; Nolan, S. P. J. Org. Chem. 2001, 66, 4094. (e) Hanna, I.; Ricard, L. Org. Lett. 2000, 2, 2651. (f) Bourgeois, D.; Pancrazi, A.; Ricard, L.; Prunet, J. Angew. Chem., Int. Ed. 2000, 39, 725. (g) Bieräugel, H.; Jansen, T. P.; Schoemaker, H. E.; Hiemstra, H.; van Maarseveen, J. H. Org. Lett. 2002, 4, 2673. (h) Fürstner, A.; Thiel, O. R.; Ackermann, L.; Schanz, H.-J.; Nolan, S. P. J. Org. Chem. 2000, 65, 2204. (i) Buijsman, R. C.; van Vuuren, E.; Sterrenburg, J. G. Org. Lett. 2001, 3, 3785. (j) Tarling, C. A.; Holmes, A. B.; Marwell, R. E. Pearson, N. D. J. Chem. Soc., Perkin Trans. 1 1999, 1695.
21. For recent papers on eight-membered ring synthesis, see: (a) Bourgeois, D.; Pancrazi, A.; Nolan, S. P.; Prunet, J. J. Organomet. Chem. 2002, 643-644, 247. (b) Ruprah, P. K.; Cros, J.-P.; Pease, J. E.; Whittingham, W. G.; Williams, J. M. J. Eur. J. Org. Chem. 2002, 3145. (c) Kariuki, B. M.; Owton, W. M.; Percy, J. M.; Pintat, S.; Smith, C. A.; Spencer, N. S.; Thomas, A. C.; Watson, M. Chem. Commun. 2002, 228. (d) Boyer, F.-D.; Hanna, I.; Nolan, S. P. J. Org. Chem. 2001, 66, 4094. (e) Hanna, I.; Ricard, L. Org. Lett. 2000, 2, 2651. (f) Bourgeois, D.; Pancrazi, A.; Ricard, L.; Prunet, J. Angew. Chem., Int. Ed. 2000, 39, 725. (g) Bieräugel, H.; Jansen, T. P.; Schoemaker, H. E.; Hiemstra, H.; van Maarseveen, J. H. Org. Lett. 2002, 4, 2673. (h) Fürstner, A.; Thiel, O. R.; Ackermann, L.; Schanz, H.-J.; Nolan, S. P. J. Org. Chem. 2000, 65, 2204. (i) Buijsman, R. C.; van Vuuren, E.; Sterrenburg, J. G. Org. Lett. 2001, 3, 3785. (j) Tarling, C. A.; Holmes, A. B.; Marwell, R. E. Pearson, N. D. J. Chem. Soc., Perkin Trans. 1 1999, 1695.
22. For recent papers on eight-membered ring synthesis, see: (a) Bourgeois, D.; Pancrazi, A.; Nolan, S. P.; Prunet, J. J. Organomet. Chem. 2002, 643-644, 247. (b) Ruprah, P. K.; Cros, J.-P.; Pease, J. E.; Whittingham, W. G.; Williams, J. M. J. Eur. J. Org. Chem. 2002, 3145. (c) Kariuki, B. M.; Owton, W. M.; Percy, J. M.; Pintat, S.; Smith, C. A.; Spencer, N. S.; Thomas, A. C.; Watson, M. Chem. Commun. 2002, 228. (d) Boyer, F.-D.; Hanna, I.; Nolan, S. P. J. Org. Chem. 2001, 66, 4094. (e) Hanna, I.; Ricard, L. Org. Lett. 2000, 2, 2651. (f) Bourgeois, D.; Pancrazi, A.; Ricard, L.; Prunet, J. Angew. Chem., Int. Ed. 2000, 39, 725. (g) Bieräugel, H.; Jansen, T. P.; Schoemaker, H. E.; Hiemstra, H.; van Maarseveen, J. H. Org. Lett. 2002, 4, 2673. (h) Fürstner, A.; Thiel, O. R.; Ackermann, L.; Schanz, H.-J.; Nolan, S. P. J. Org. Chem. 2000, 65, 2204. (i) Buijsman, R. C.; van Vuuren, E.; Sterrenburg, J. G. Org. Lett. 2001, 3, 3785. (j) Tarling, C. A.; Holmes, A. B.; Marwell, R. E. Pearson, N. D. J. Chem. Soc., Perkin Trans. 1 1999, 1695.
23. For recent papers on eight-membered ring synthesis, see: (a) Bourgeois, D.; Pancrazi, A.; Nolan, S. P.; Prunet, J. J. Organomet. Chem. 2002, 643-644, 247. (b) Ruprah, P. K.; Cros, J.-P.; Pease, J. E.; Whittingham, W. G.; Williams, J. M. J. Eur. J. Org. Chem. 2002, 3145. (c) Kariuki, B. M.; Owton, W. M.; Percy, J. M.; Pintat, S.; Smith, C. A.; Spencer, N. S.; Thomas, A. C.; Watson, M. Chem. Commun. 2002, 228. (d) Boyer, F.-D.; Hanna, I.; Nolan, S. P. J. Org. Chem. 2001, 66, 4094. (e) Hanna, I.; Ricard, L. Org. Lett. 2000, 2, 2651. (f) Bourgeois, D.; Pancrazi, A.; Ricard, L.; Prunet, J. Angew. Chem., Int. Ed. 2000, 39, 725. (g) Bieräugel, H.; Jansen, T. P.; Schoemaker, H. E.; Hiemstra, H.; van Maarseveen, J. H. Org. Lett. 2002, 4, 2673. (h) Fürstner, A.; Thiel, O. R.; Ackermann, L.; Schanz, H.-J.; Nolan, S. P. J. Org. Chem. 2000, 65, 2204. (i) Buijsman, R. C.; van Vuuren, E.; Sterrenburg, J. G. Org. Lett. 2001, 3, 3785. (j) Tarling, C. A.; Holmes, A. B.; Marwell, R. E. Pearson, N. D. J. Chem. Soc., Perkin Trans. 1 1999, 1695.
24. For recent papers on eight-membered ring synthesis, see: (a) Bourgeois, D.; Pancrazi, A.; Nolan, S. P.; Prunet, J. J. Organomet. Chem. 2002, 643-644, 247. (b) Ruprah, P. K.; Cros, J.-P.; Pease, J. E.; Whittingham, W. G.; Williams, J. M. J. Eur. J. Org. Chem. 2002, 3145. (c) Kariuki, B. M.; Owton, W. M.; Percy, J. M.; Pintat, S.; Smith, C. A.; Spencer, N. S.; Thomas, A. C.; Watson, M. Chem. Commun. 2002, 228. (d) Boyer, F.-D.; Hanna, I.; Nolan, S. P. J. Org. Chem. 2001, 66, 4094. (e) Hanna, I.; Ricard, L. Org. Lett. 2000, 2, 2651. (f) Bourgeois, D.; Pancrazi, A.; Ricard, L.; Prunet, J. Angew. Chem., Int. Ed. 2000, 39, 725. (g) Bieräugel, H.; Jansen, T. P.; Schoemaker, H. E.; Hiemstra, H.; van Maarseveen, J. H. Org. Lett. 2002, 4, 2673. (h) Fürstner, A.; Thiel, O. R.; Ackermann, L.; Schanz, H.-J.; Nolan, S. P. J. Org. Chem. 2000, 65, 2204. (i) Buijsman, R. C.; van Vuuren, E.; Sterrenburg, J. G. Org. Lett. 2001, 3, 3785. (j) Tarling, C. A.; Holmes, A. B.; Marwell, R. E. Pearson, N. D. J. Chem. Soc., Perkin Trans. 1 1999, 1695.
25. For recent papers on eight-membered ring synthesis, see: (a) Bourgeois, D.; Pancrazi, A.; Nolan, S. P.; Prunet, J. J. Organomet. Chem. 2002, 643-644, 247. (b) Ruprah, P. K.; Cros, J.-P.; Pease, J. E.; Whittingham, W. G.; Williams, J. M. J. Eur. J. Org. Chem. 2002, 3145. (c) Kariuki, B. M.; Owton, W. M.; Percy, J. M.; Pintat, S.; Smith, C. A.; Spencer, N. S.; Thomas, A. C.; Watson, M. Chem. Commun. 2002, 228. (d) Boyer, F.-D.; Hanna, I.; Nolan, S. P. J. Org. Chem. 2001, 66, 4094. (e) Hanna, I.; Ricard, L. Org. Lett. 2000, 2, 2651. (f) Bourgeois, D.; Pancrazi, A.; Ricard, L.; Prunet, J. Angew. Chem., Int. Ed. 2000, 39, 725. (g) Bieräugel, H.; Jansen, T. P.; Schoemaker, H. E.; Hiemstra, H.; van Maarseveen, J. H. Org. Lett. 2002, 4, 2673. (h) Fürstner, A.; Thiel, O. R.; Ackermann, L.; Schanz, H.-J.; Nolan, S. P. J. Org. Chem. 2000, 65, 2204. (i) Buijsman, R. C.; van Vuuren, E.; Sterrenburg, J. G. Org. Lett. 2001, 3, 3785. (j) Tarling, C. A.; Holmes, A. B.; Marwell, R. E. Pearson, N. D. J. Chem. Soc., Perkin Trans. 1 1999, 1695.
26. For recent papers on eight-membered ring synthesis, see: (a) Bourgeois, D.; Pancrazi, A.; Nolan, S. P.; Prunet, J. J. Organomet. Chem. 2002, 643-644, 247. (b) Ruprah, P. K.; Cros, J.-P.; Pease, J. E.; Whittingham, W. G.; Williams, J. M. J. Eur. J. Org. Chem. 2002, 3145. (c) Kariuki, B. M.; Owton, W. M.; Percy, J. M.; Pintat, S.; Smith, C. A.; Spencer, N. S.; Thomas, A. C.; Watson, M. Chem. Commun. 2002, 228. (d) Boyer, F.-D.; Hanna, I.; Nolan, S. P. J. Org. Chem. 2001, 66, 4094. (e) Hanna, I.; Ricard, L. Org. Lett. 2000, 2, 2651. (f) Bourgeois, D.; Pancrazi, A.; Ricard, L.; Prunet, J. Angew. Chem., Int. Ed. 2000, 39, 725. (g) Bieräugel, H.; Jansen, T. P.; Schoemaker, H. E.; Hiemstra, H.; van Maarseveen, J. H. Org. Lett. 2002, 4, 2673. (h) Fürstner, A.; Thiel, O. R.; Ackermann, L.; Schanz, H.-J.; Nolan, S. P. J. Org. Chem. 2000, 65, 2204. (i) Buijsman, R. C.; van Vuuren, E.; Sterrenburg, J. G. Org. Lett. 2001, 3, 3785. (j) Tarling, C. A.; Holmes, A. B.; Marwell, R. E. Pearson, N. D. J. Chem. Soc., Perkin Trans. 1 1999, 1695.
27. Catalysts 1, 2, 3, and 4 are commercially available. Catalyst 5: Kingsbury, J. S.; Harrity, J. P. A.; Bonitatebus, P. J., Jr.; Hoveyda, J. Am. Chem. Soc. 1999, 121, 791. Catalyst 6: Wakamatsu, H.; Blechert, S. Angew. Chem., Int. Ed. 2002, 41, 794. Catalyst 7: Rolle, T.; Grubbs, R. H. Chem. Commun. 2002, 1070. Catalyst 8: Grela, K.; Harutyunyan, S.; Michrowska, A. Angew. Chem., Int. Ed. 2002, 41, 4038.
28. Catalysts 1, 2, 3, and 4 are commercially available. Catalyst 5: Kingsbury, J. S.; Harrity, J. P. A.; Bonitatebus, P. J., Jr.; Hoveyda, J. Am. Chem. Soc. 1999, 121, 791. Catalyst 6: Wakamatsu, H.; Blechert, S. Angew. Chem., Int. Ed. 2002, 41, 794. Catalyst 7: Rolle, T.; Grubbs, R. H. Chem. Commun. 2002, 1070. Catalyst 8: Grela, K.; Harutyunyan, S.; Michrowska, A. Angew. Chem., Int. Ed. 2002, 41, 4038.
29. Catalysts 1, 2, 3, and 4 are commercially available. Catalyst 5: Kingsbury, J. S.; Harrity, J. P. A.; Bonitatebus, P. J., Jr.; Hoveyda, J. Am. Chem. Soc. 1999, 121, 791. Catalyst 6: Wakamatsu, H.; Blechert, S. Angew. Chem., Int. Ed. 2002, 41, 794. Catalyst 7: Rolle, T.; Grubbs, R. H. Chem. Commun. 2002, 1070. Catalyst 8: Grela, K.; Harutyunyan, S.; Michrowska, A. Angew. Chem., Int. Ed. 2002, 41, 4038.
30. Catalysts 1, 2, 3, and 4 are commercially available. Catalyst 5: Kingsbury, J. S.; Harrity, J. P. A.; Bonitatebus, P. J., Jr.; Hoveyda, J. Am. Chem. Soc. 1999, 121, 791. Catalyst 6: Wakamatsu, H.; Blechert, S. Angew. Chem., Int. Ed. 2002, 41, 794. Catalyst 7: Rolle, T.; Grubbs, R. H. Chem. Commun. 2002, 1070. Catalyst 8: Grela, K.; Harutyunyan, S.; Michrowska, A. Angew. Chem., Int. Ed. 2002, 41, 4038.
31. Crimmins has shown that conformational effects play a key role in the RCM reactions leading to eight-membered rings. See: Crimmins, M. T.; Choy, A. J. J. Am. Chem. Soc. 1999, 121, 5653. A detailed analysis of conformational effects on cyclization in our work will be presented in a full paper.
32. Randl, S.; Gessler, S.; Wakamatsu, H.; Blechert, S. Synlett 2001, 430.
33. Orita, A.; Nagano, Y.; Hirano, J.; Otera, J. Synlett 2001, 637.
34. Yamamoto, K.; Biswas, K.; Gaul, C.; Danishefsky, S. J. Tetrahedron Lett. 2003, 44, 3297.
35. Cho, J. H.; Kim, B. M. Org. Lett. 2003, 5, 531.
36. (a) Petasis, N. A.; Patane, M. A. Tetrahedron 1992, 48, 5757.
37. For selected synthetic effort, see: (b) Rowley, M.; Tsukamoto, M.; Kishi, Y. J. Am. Chem. Soc. 1989, 111, 2735. (c) Snider, B. B.; Yang, K. J. Org. Chem. 1992, 57, 3615. (d) Paquette, L. A.; Wang, T. Z.; Vo, N. H. J. Am. Chem. Soc. 1993, 115, 1676. (e) Ruprah, P. K.; Cros, J.-P.; Pease, J. E.; Whittingham, W. G.; Williams, J. M. J. Eur. J. Org. Chem. 2002, 3145.
38. For selected synthetic effort, see: (b) Rowley, M.; Tsukamoto, M.; Kishi, Y. J. Am. Chem. Soc. 1989, 111, 2735. (c) Snider, B. B.; Yang, K. J. Org. Chem. 1992, 57, 3615. (d) Paquette, L. A.; Wang, T. Z.; Vo, N. H. J. Am. Chem. Soc. 1993, 115, 1676. (e) Ruprah, P. K.; Cros, J.-P.; Pease, J. E.; Whittingham, W. G.; Williams, J. M. J. Eur. J. Org. Chem. 2002, 3145.
39. For selected synthetic effort, see: (b) Rowley, M.; Tsukamoto, M.; Kishi, Y. J. Am. Chem. Soc. 1989, 111, 2735. (c) Snider, B. B.; Yang, K. J. Org. Chem. 1992, 57, 3615. (d) Paquette, L. A.; Wang, T. Z.; Vo, N. H. J. Am. Chem. Soc. 1993, 115, 1676. (e) Ruprah, P. K.; Cros, J.-P.; Pease, J. E.; Whittingham, W. G.; Williams, J. M. J. Eur. J. Org. Chem. 2002, 3145.
40. For selected synthetic effort, see: (b) Rowley, M.; Tsukamoto, M.; Kishi, Y. J. Am. Chem. Soc. 1989, 111, 2735. (c) Snider, B. B.; Yang, K. J. Org. Chem. 1992, 57, 3615. (d) Paquette, L. A.; Wang, T. Z.; Vo, N. H. J. Am. Chem. Soc. 1993, 115, 1676. (e) Ruprah, P. K.; Cros, J.-P.; Pease, J. E.; Whittingham, W. G.; Williams, J. M. J. Eur. J. Org. Chem. 2002, 3145.
41. (a) Curran, D. P.; Porter, N. A.; Giese, B. Stereochemistry of Radical Reactions, VCH: Weinheim, 1995.
42. (b) Also see ref 1.