Synthesis of Heterocyclic and Carbocyclic Fluoro-olefins by Ring-Closing Metathesis

Organic Letters

Volumn 5, Issue 19, 2003, Pages 3403-3406

  Salim, Sofia S ^a   Bellingham, Richard K ^b   Satcharoen, Vachiraporn ^a   Brown, Richard C D ^a  

^a UNIVERSITY OF SOUTHAMPTON   (United Kingdom)

^b GLAXOSMITHKLINE   (United Kingdom)

Author keywords

[No Author keywords available]

Indexed keywords

ALKENE; ALKENE DERIVATIVE; AMINE; FLUORIDE; HETEROCYCLIC COMPOUND; RUTHENIUM ALKYLIDENE CARBENE; RUTHENIUM DERIVATIVE; SULFAMIDE DERIVATIVE; UNCLASSIFIED DRUG;

ARTICLE; COMMERCIAL PHENOMENA; RING CLOSING METATHESIS; SYNTHESIS;

EID: 0344824466     PISSN: 15237060     EISSN: None     Source Type: Journal    
DOI: 10.1021/ol035065w     Document Type: Article

References (46)

1. For fluoro-olefin isosteres: Zhao, K.; Lim, D. S.; Funaki, T.; Welch, J. T. Bioorg. Med. Chem. 2003, 11, 207. Bartlett, P. A.; Otake, A. J. Org. Chem. 1995, 60, 3107. Veenstra, S. J.; Hauser, K.; Felber, P. Bioorg. Med. Chem. Lett. 1997, 7, 351. Welch, J. T.; Lin, J. Tetrahedron 1996, 52, 291. Allmendinger, T.; Felder, E.; Hungerbühler, E. Tetrahedron Lett. 1990, 31, 7297. Allmendinger, T.; Furet, P.; Hungerbühler, E. Tetrahedron Lett. 1990, 31, 7301. Abraham, R. J.; Ellison, S. L. R.; Schonholzer, P.; Thomas, W. A. Tetrahedron 1986, 42, 2101.
2. For fluoro-olefin isosteres: Zhao, K.; Lim, D. S.; Funaki, T.; Welch, J. T. Bioorg. Med. Chem. 2003, 11, 207. Bartlett, P. A.; Otake, A. J. Org. Chem. 1995, 60, 3107. Veenstra, S. J.; Hauser, K.; Felber, P. Bioorg. Med. Chem. Lett. 1997, 7, 351. Welch, J. T.; Lin, J. Tetrahedron 1996, 52, 291. Allmendinger, T.; Felder, E.; Hungerbühler, E. Tetrahedron Lett. 1990, 31, 7297. Allmendinger, T.; Furet, P.; Hungerbühler, E. Tetrahedron Lett. 1990, 31, 7301. Abraham, R. J.; Ellison, S. L. R.; Schonholzer, P.; Thomas, W. A. Tetrahedron 1986, 42, 2101.
3. For fluoro-olefin isosteres: Zhao, K.; Lim, D. S.; Funaki, T.; Welch, J. T. Bioorg. Med. Chem. 2003, 11, 207. Bartlett, P. A.; Otake, A. J. Org. Chem. 1995, 60, 3107. Veenstra, S. J.; Hauser, K.; Felber, P. Bioorg. Med. Chem. Lett. 1997, 7, 351. Welch, J. T.; Lin, J. Tetrahedron 1996, 52, 291. Allmendinger, T.; Felder, E.; Hungerbühler, E. Tetrahedron Lett. 1990, 31, 7297. Allmendinger, T.; Furet, P.; Hungerbühler, E. Tetrahedron Lett. 1990, 31, 7301. Abraham, R. J.; Ellison, S. L. R.; Schonholzer, P.; Thomas, W. A. Tetrahedron 1986, 42, 2101.
4. For fluoro-olefin isosteres: Zhao, K.; Lim, D. S.; Funaki, T.; Welch, J. T. Bioorg. Med. Chem. 2003, 11, 207. Bartlett, P. A.; Otake, A. J. Org. Chem. 1995, 60, 3107. Veenstra, S. J.; Hauser, K.; Felber, P. Bioorg. Med. Chem. Lett. 1997, 7, 351. Welch, J. T.; Lin, J. Tetrahedron 1996, 52, 291. Allmendinger, T.; Felder, E.; Hungerbühler, E. Tetrahedron Lett. 1990, 31, 7297. Allmendinger, T.; Furet, P.; Hungerbühler, E. Tetrahedron Lett. 1990, 31, 7301. Abraham, R. J.; Ellison, S. L. R.; Schonholzer, P.; Thomas, W. A. Tetrahedron 1986, 42, 2101.
5. For fluoro-olefin isosteres: Zhao, K.; Lim, D. S.; Funaki, T.; Welch, J. T. Bioorg. Med. Chem. 2003, 11, 207. Bartlett, P. A.; Otake, A. J. Org. Chem. 1995, 60, 3107. Veenstra, S. J.; Hauser, K.; Felber, P. Bioorg. Med. Chem. Lett. 1997, 7, 351. Welch, J. T.; Lin, J. Tetrahedron 1996, 52, 291. Allmendinger, T.; Felder, E.; Hungerbühler, E. Tetrahedron Lett. 1990, 31, 7297. Allmendinger, T.; Furet, P.; Hungerbühler, E. Tetrahedron Lett. 1990, 31, 7301. Abraham, R. J.; Ellison, S. L. R.; Schonholzer, P.; Thomas, W. A. Tetrahedron 1986, 42, 2101.
6. For fluoro-olefin isosteres: Zhao, K.; Lim, D. S.; Funaki, T.; Welch, J. T. Bioorg. Med. Chem. 2003, 11, 207. Bartlett, P. A.; Otake, A. J. Org. Chem. 1995, 60, 3107. Veenstra, S. J.; Hauser, K.; Felber, P. Bioorg. Med. Chem. Lett. 1997, 7, 351. Welch, J. T.; Lin, J. Tetrahedron 1996, 52, 291. Allmendinger, T.; Felder, E.; Hungerbühler, E. Tetrahedron Lett. 1990, 31, 7297. Allmendinger, T.; Furet, P.; Hungerbühler, E. Tetrahedron Lett. 1990, 31, 7301. Abraham, R. J.; Ellison, S. L. R.; Schonholzer, P.; Thomas, W. A. Tetrahedron 1986, 42, 2101.
7. For fluoro-olefin isosteres: Zhao, K.; Lim, D. S.; Funaki, T.; Welch, J. T. Bioorg. Med. Chem. 2003, 11, 207. Bartlett, P. A.; Otake, A. J. Org. Chem. 1995, 60, 3107. Veenstra, S. J.; Hauser, K.; Felber, P. Bioorg. Med. Chem. Lett. 1997, 7, 351. Welch, J. T.; Lin, J. Tetrahedron 1996, 52, 291. Allmendinger, T.; Felder, E.; Hungerbühler, E. Tetrahedron Lett. 1990, 31, 7297. Allmendinger, T.; Furet, P.; Hungerbühler, E. Tetrahedron Lett. 1990, 31, 7301. Abraham, R. J.; Ellison, S. L. R.; Schonholzer, P.; Thomas, W. A. Tetrahedron 1986, 42, 2101.
8. Gardner, R. R.; Liang, G.-B.; Gellman, S. H. J. Am. Chem. Soc. 1999, 121, 1806. Wipf, P.; Henningger, T. C.; Geib, S. J. J. Org. Chem. 1998, 63, 6088. Cox, M. T.; Gormley, J. J.; Hayward, C. F.; Petter, N. N. Chem. Commun. 1980, 800. Cox, M. T.; Heaton, D. W.; Horbury, J. Chem. Commun. 1980, 799. Hann, M. M.; Sammes, P. G.; Kennewell, P. D.; Taylor, J. B. Chem. Commun. 1980, 234.
9. Gardner, R. R.; Liang, G.-B.; Gellman, S. H. J. Am. Chem. Soc. 1999, 121, 1806. Wipf, P.; Henningger, T. C.; Geib, S. J. J. Org. Chem. 1998, 63, 6088. Cox, M. T.; Gormley, J. J.; Hayward, C. F.; Petter, N. N. Chem. Commun. 1980, 800. Cox, M. T.; Heaton, D. W.; Horbury, J. Chem. Commun. 1980, 799. Hann, M. M.; Sammes, P. G.; Kennewell, P. D.; Taylor, J. B. Chem. Commun. 1980, 234.
10. Gardner, R. R.; Liang, G.-B.; Gellman, S. H. J. Am. Chem. Soc. 1999, 121, 1806. Wipf, P.; Henningger, T. C.; Geib, S. J. J. Org. Chem. 1998, 63, 6088. Cox, M. T.; Gormley, J. J.; Hayward, C. F.; Petter, N. N. Chem. Commun. 1980, 800. Cox, M. T.; Heaton, D. W.; Horbury, J. Chem. Commun. 1980, 799. Hann, M. M.; Sammes, P. G.; Kennewell, P. D.; Taylor, J. B. Chem. Commun. 1980, 234.
11. Gardner, R. R.; Liang, G.-B.; Gellman, S. H. J. Am. Chem. Soc. 1999, 121, 1806. Wipf, P.; Henningger, T. C.; Geib, S. J. J. Org. Chem. 1998, 63, 6088. Cox, M. T.; Gormley, J. J.; Hayward, C. F.; Petter, N. N. Chem. Commun. 1980, 800. Cox, M. T.; Heaton, D. W.; Horbury, J. Chem. Commun. 1980, 799. Hann, M. M.; Sammes, P. G.; Kennewell, P. D.; Taylor, J. B. Chem. Commun. 1980, 234.
12. Gardner, R. R.; Liang, G.-B.; Gellman, S. H. J. Am. Chem. Soc. 1999, 121, 1806. Wipf, P.; Henningger, T. C.; Geib, S. J. J. Org. Chem. 1998, 63, 6088. Cox, M. T.; Gormley, J. J.; Hayward, C. F.; Petter, N. N. Chem. Commun. 1980, 800. Cox, M. T.; Heaton, D. W.; Horbury, J. Chem. Commun. 1980, 799. Hann, M. M.; Sammes, P. G.; Kennewell, P. D.; Taylor, J. B. Chem. Commun. 1980, 234.
13. For general reviews of peptidomimetics: Hanessian, S.; McNaughton-Smith, G.; Lombart, H.-G.; Lubell, W. D. Tetrahedron 1997, 53, 12789. Gante, J. Angew. Chem., Int. Ed. Engl. 1994, 33, 1699. Gainnis, A.; Kolter, T. Angew. Chem., Int. Ed. Engl. 1993, 32, 1244.
14. For general reviews of peptidomimetics: Hanessian, S.; McNaughton-Smith, G.; Lombart, H.-G.; Lubell, W. D. Tetrahedron 1997, 53, 12789. Gante, J. Angew. Chem., Int. Ed. Engl. 1994, 33, 1699. Gainnis, A.; Kolter, T. Angew. Chem., Int. Ed. Engl. 1993, 32, 1244.
15. For general reviews of peptidomimetics: Hanessian, S.; McNaughton-Smith, G.; Lombart, H.-G.; Lubell, W. D. Tetrahedron 1997, 53, 12789. Gante, J. Angew. Chem., Int. Ed. Engl. 1994, 33, 1699. Gainnis, A.; Kolter, T. Angew. Chem., Int. Ed. Engl. 1993, 32, 1244.
16. For reviews on the synthesis of fluoro-olefins: Gouverneur, V.; Greedy, B. Chem. Eur. J. 2002, 8, 766. Taylor, S. D.; Kotoris, C. C.; Hum, G. Tetrahedron 1999, 55, 12431. Silvester, M. J. Aldrichimica Acta 1995, 28, 45. See also ref 1 for selected examples.
17. For reviews on the synthesis of fluoro-olefins: Gouverneur, V.; Greedy, B. Chem. Eur. J. 2002, 8, 766. Taylor, S. D.; Kotoris, C. C.; Hum, G. Tetrahedron 1999, 55, 12431. Silvester, M. J. Aldrichimica Acta 1995, 28, 45. See also ref 1 for selected examples.
18. For reviews on the synthesis of fluoro-olefins: Gouverneur, V.; Greedy, B. Chem. Eur. J. 2002, 8, 766. Taylor, S. D.; Kotoris, C. C.; Hum, G. Tetrahedron 1999, 55, 12431. Silvester, M. J. Aldrichimica Acta 1995, 28, 45. See also ref 1 for selected examples.
19. For general reviews of olefin metathesis: (a) Grubbs, R. H.; Miller, S. J.; Fu, G. C. Acc. Chem. Res. 1995, 28, 446. (b) Schuster, M.; Blechert S. Angew. Chem., Int. Ed. Engl. 1997, 36, 2037. (c) Armstrong, S. K. J. Chem. Soc., Perkin Trans. 1 1998, 371. (d) Phillips, A. J.; Abell, A. D. Aldrichimica Acta 1999, 32, 75. (e) Fürstner A. Angew. Chem., Int. Ed. 2000, 39, 3012. (f) Connon, S. J.; Blechert, S. Angew. Chem., Int. Ed. 2003, 42, 1900.
20. For general reviews of olefin metathesis: (a) Grubbs, R. H.; Miller, S. J.; Fu, G. C. Acc. Chem. Res. 1995, 28, 446. (b) Schuster, M.; Blechert S. Angew. Chem., Int. Ed. Engl. 1997, 36, 2037. (c) Armstrong, S. K. J. Chem. Soc., Perkin Trans. 1 1998, 371. (d) Phillips, A. J.; Abell, A. D. Aldrichimica Acta 1999, 32, 75. (e) Fürstner A. Angew. Chem., Int. Ed. 2000, 39, 3012. (f) Connon, S. J.; Blechert, S. Angew. Chem., Int. Ed. 2003, 42, 1900.
21. For general reviews of olefin metathesis: (a) Grubbs, R. H.; Miller, S. J.; Fu, G. C. Acc. Chem. Res. 1995, 28, 446. (b) Schuster, M.; Blechert S. Angew. Chem., Int. Ed. Engl. 1997, 36, 2037. (c) Armstrong, S. K. J. Chem. Soc., Perkin Trans. 1 1998, 371. (d) Phillips, A. J.; Abell, A. D. Aldrichimica Acta 1999, 32, 75. (e) Fürstner A. Angew. Chem., Int. Ed. 2000, 39, 3012. (f) Connon, S. J.; Blechert, S. Angew. Chem., Int. Ed. 2003, 42, 1900.
22. For general reviews of olefin metathesis: (a) Grubbs, R. H.; Miller, S. J.; Fu, G. C. Acc. Chem. Res. 1995, 28, 446. (b) Schuster, M.; Blechert S. Angew. Chem., Int. Ed. Engl. 1997, 36, 2037. (c) Armstrong, S. K. J. Chem. Soc., Perkin Trans. 1 1998, 371. (d) Phillips, A. J.; Abell, A. D. Aldrichimica Acta 1999, 32, 75. (e) Fürstner A. Angew. Chem., Int. Ed. 2000, 39, 3012. (f) Connon, S. J.; Blechert, S. Angew. Chem., Int. Ed. 2003, 42, 1900.
23. For general reviews of olefin metathesis: (a) Grubbs, R. H.; Miller, S. J.; Fu, G. C. Acc. Chem. Res. 1995, 28, 446. (b) Schuster, M.; Blechert S. Angew. Chem., Int. Ed. Engl. 1997, 36, 2037. (c) Armstrong, S. K. J. Chem. Soc., Perkin Trans. 1 1998, 371. (d) Phillips, A. J.; Abell, A. D. Aldrichimica Acta 1999, 32, 75. (e) Fürstner A. Angew. Chem., Int. Ed. 2000, 39, 3012. (f) Connon, S. J.; Blechert, S. Angew. Chem., Int. Ed. 2003, 42, 1900.
24. For general reviews of olefin metathesis: (a) Grubbs, R. H.; Miller, S. J.; Fu, G. C. Acc. Chem. Res. 1995, 28, 446. (b) Schuster, M.; Blechert S. Angew. Chem., Int. Ed. Engl. 1997, 36, 2037. (c) Armstrong, S. K. J. Chem. Soc., Perkin Trans. 1 1998, 371. (d) Phillips, A. J.; Abell, A. D. Aldrichimica Acta 1999, 32, 75. (e) Fürstner A. Angew. Chem., Int. Ed. 2000, 39, 3012. (f) Connon, S. J.; Blechert, S. Angew. Chem., Int. Ed. 2003, 42, 1900.
25. 2), see ref 10 and: Hultén, J.; Bonham, N. M.; Nillroth, U.; Hansson, T.; Zuccarello, G.; Bouzide, A.; Åqvist, J.; Classon, B.; Danielson, U. H.; Karlén, A. ; Kvarnström, I.; Samuelsson, B.; Hallberg, A. J. Med. Chem. 1997, 40, 885. Bäckbro, K.; Löwgren, S.; Österlund, K.; Atepo, J.; Unge, T.; Hultén, J.; Bonham, N. M.; Schaal, W.; Karlén, A.; Hallberg, A. J. Med. Chem. 1997, 40, 898. Triazacyclic ureas 2: Sham, H. L.; Zhao, C.; Stewart, K. D.; Betebenner, D. A.; Lin, S.; Park, C. H.; Kong, X.-P.; Rosenbrook, W. Jr.; Herrin, T.; Madigan, D.; Vasavanonda, S.; Lyons, N.; Molla, A.; Kempf, D. J.; Plattner, J. J.; Norbeck, D. W. J. Med. Chem. 1996, 39, 392.
26. 2), see ref 10 and: Hultén, J.; Bonham, N. M.; Nillroth, U.; Hansson, T.; Zuccarello, G.; Bouzide, A.; Åqvist, J.; Classon, B.; Danielson, U. H.; Karlén, A. ; Kvarnström, I.; Samuelsson, B.; Hallberg, A. J. Med. Chem. 1997, 40, 885. Bäckbro, K.; Löwgren, S.; Österlund, K.; Atepo, J.; Unge, T.; Hultén, J.; Bonham, N. M.; Schaal, W.; Karlén, A.; Hallberg, A. J. Med. Chem. 1997, 40, 898. Triazacyclic ureas 2: Sham, H. L.; Zhao, C.; Stewart, K. D.; Betebenner, D. A.; Lin, S.; Park, C. H.; Kong, X.-P.; Rosenbrook, W. Jr.; Herrin, T.; Madigan, D.; Vasavanonda, S.; Lyons, N.; Molla, A.; Kempf, D. J.; Plattner, J. J.; Norbeck, D. W. J. Med. Chem. 1996, 39, 392.
27. 2), see ref 10 and: Hultén, J.; Bonham, N. M.; Nillroth, U.; Hansson, T.; Zuccarello, G.; Bouzide, A.; Åqvist, J.; Classon, B.; Danielson, U. H.; Karlén, A. ; Kvarnström, I.; Samuelsson, B.; Hallberg, A. J. Med. Chem. 1997, 40, 885. Bäckbro, K.; Löwgren, S.; Österlund, K.; Atepo, J.; Unge, T.; Hultén, J.; Bonham, N. M.; Schaal, W.; Karlén, A.; Hallberg, A. J. Med. Chem. 1997, 40, 898. Triazacyclic ureas 2: Sham, H. L.; Zhao, C.; Stewart, K. D.; Betebenner, D. A.; Lin, S.; Park, C. H.; Kong, X.-P.; Rosenbrook, W. Jr.; Herrin, T.; Madigan, D.; Vasavanonda, S.; Lyons, N.; Molla, A.; Kempf, D. J.; Plattner, J. J.; Norbeck, D. W. J. Med. Chem. 1996, 39, 392.
28. 2), see ref 10 and: Hultén, J.; Bonham, N. M.; Nillroth, U.; Hansson, T.; Zuccarello, G.; Bouzide, A.; Åqvist, J.; Classon, B.; Danielson, U. H.; Karlén, A. ; Kvarnström, I.; Samuelsson, B.; Hallberg, A. J. Med. Chem. 1997, 40, 885. Bäckbro, K.; Löwgren, S.; Österlund, K.; Atepo, J.; Unge, T.; Hultén, J.; Bonham, N. M.; Schaal, W.; Karlén, A.; Hallberg, A. J. Med. Chem. 1997, 40, 898. Triazacyclic ureas 2: Sham, H. L.; Zhao, C.; Stewart, K. D.; Betebenner, D. A.; Lin, S.; Park, C. H.; Kong, X.-P.; Rosenbrook, W. Jr.; Herrin, T.; Madigan, D.; Vasavanonda, S.; Lyons, N.; Molla, A.; Kempf, D. J.; Plattner, J. J.; Norbeck, D. W. J. Med. Chem. 1996, 39, 392.
29. 2), see ref 10 and: Hultén, J.; Bonham, N. M.; Nillroth, U.; Hansson, T.; Zuccarello, G.; Bouzide, A.; Åqvist, J.; Classon, B.; Danielson, U. H.; Karlén, A. ; Kvarnström, I.; Samuelsson, B.; Hallberg, A. J. Med. Chem. 1997, 40, 885. Bäckbro, K.; Löwgren, S.; Österlund, K.; Atepo, J.; Unge, T.; Hultén, J.; Bonham, N. M.; Schaal, W.; Karlén, A.; Hallberg, A. J. Med. Chem. 1997, 40, 898. Triazacyclic ureas 2: Sham, H. L.; Zhao, C.; Stewart, K. D.; Betebenner, D. A.; Lin, S.; Park, C. H.; Kong, X.-P.; Rosenbrook, W. Jr.; Herrin, T.; Madigan, D.; Vasavanonda, S.; Lyons, N.; Molla, A.; Kempf, D. J.; Plattner, J. J.; Norbeck, D. W. J. Med. Chem. 1996, 39, 392.
30. For olefin RCM approaches to sulfamides: Dougherty, J. M.; Probst, D. A. ; Robinson, R. E.; Moore, J. D.; Klein, T. A.; Snelgrove, K. A.; Hanson, P. R. Tetrahedron 2000, 56, 9781.
31. For olefin RCM approaches to related (S)-heterocycles: Cyclic sulfonamides (sultams): (a) Hanson, P. R.; Probst, D. A.; Robinson, R. E.; Yau, M. Tetrahedron Lett. 1999, 40, 4761. (b) Brown, R. C. D.; Castro, J. L.; Moriggi, J. D. Tetrahedron Lett. 2000, 41, 3681. (c) Long, D. D.; Termin, A. P. Tetrahedron Lett. 2000, 41, 6743. Sultones: (d) Karsch, S.; Schwab, P.; Metz, P. Synlett 2002, 2019.
32. For olefin RCM approaches to related (S)-heterocycles: Cyclic sulfonamides (sultams): (a) Hanson, P. R.; Probst, D. A.; Robinson, R. E.; Yau, M. Tetrahedron Lett. 1999, 40, 4761. (b) Brown, R. C. D.; Castro, J. L.; Moriggi, J. D. Tetrahedron Lett. 2000, 41, 3681. (c) Long, D. D.; Termin, A. P. Tetrahedron Lett. 2000, 41, 6743. Sultones: (d) Karsch, S.; Schwab, P.; Metz, P. Synlett 2002, 2019.
33. For olefin RCM approaches to related (S)-heterocycles: Cyclic sulfonamides (sultams): (a) Hanson, P. R.; Probst, D. A.; Robinson, R. E.; Yau, M. Tetrahedron Lett. 1999, 40, 4761. (b) Brown, R. C. D.; Castro, J. L.; Moriggi, J. D. Tetrahedron Lett. 2000, 41, 3681. (c) Long, D. D.; Termin, A. P. Tetrahedron Lett. 2000, 41, 6743. Sultones: (d) Karsch, S.; Schwab, P.; Metz, P. Synlett 2002, 2019.
34. For olefin RCM approaches to related (S)-heterocycles: Cyclic sulfonamides (sultams): (a) Hanson, P. R.; Probst, D. A.; Robinson, R. E.; Yau, M. Tetrahedron Lett. 1999, 40, 4761. (b) Brown, R. C. D.; Castro, J. L.; Moriggi, J. D. Tetrahedron Lett. 2000, 41, 3681. (c) Long, D. D.; Termin, A. P. Tetrahedron Lett. 2000, 41, 6743. Sultones: (d) Karsch, S.; Schwab, P.; Metz, P. Synlett 2002, 2019.
35. De Lucca, G. V. J. Org. Chem. 1998, 63, 4755.
36. See ref 7 and: Dewynter, G.; Aouf, N.; Criton, M.; Montero J. L. Tetrahedron 1993, 49, 65.
37. 4S): calcd, 379.1098; found, 379.1099.
38. Imhof, S.; Randl, S.; Blechert, S. Chem. Commun. 2001, 1692.
39. Chatterjee, A. K.; Morgan, J. P.; Scholl, M.; Grubbs, R. H. J. Am. Chem. Soc. 2000, 122, 3783. See also: Kirkland, T. A.; Grubbs, R. H. J. Org. Chem. 1997, 62, 7310.
40. Chatterjee, A. K.; Morgan, J. P.; Scholl, M.; Grubbs, R. H. J. Am. Chem. Soc. 2000, 122, 3783. See also: Kirkland, T. A.; Grubbs, R. H. J. Org. Chem. 1997, 62, 7310.
41. RCM of chloro-olefins has recently been realized using the ruthenium complex 11 to provide five-to seven-membered products. Chao, W.; Weinreb, S. M. Org. Lett. 2003, 5, 2505.
42. Garber, S. B.; Kingsbury, J. S.; Gray, B. L.; Hoveyda, A. H. J. Am. Chem. Soc. 2000, 122, 8168.
43. Early reports in the literature suggested that RCM reactions of substrates containing free basic nitrogen atoms could be problematic, whereas the corresponding ammonium salts could be cyclized. Fu, G. C.; Nguyen, S. T.; Grubbs, R. H. J. Am. Chem. Soc. 1993, 115, 9856. Felpin, F.-X.; Girard, S.; Vo-Thanh, G.; Robins, R. J.; Villiéras, J.; Lebreton, J. J. Org. Chem. 2001, 66, 6305. In the current work, we initially formed TFA salts of 17 and 19 prior to submission to the RCM conditions but subsequently found that the reactions of free amines 17 and 19 with ruthenium complex 11 gave similar results.
44. Early reports in the literature suggested that RCM reactions of substrates containing free basic nitrogen atoms could be problematic, whereas the corresponding ammonium salts could be cyclized. Fu, G. C.; Nguyen, S. T.; Grubbs, R. H. J. Am. Chem. Soc. 1993, 115, 9856. Felpin, F.-X.; Girard, S.; Vo-Thanh, G.; Robins, R. J.; Villiéras, J.; Lebreton, J. J. Org. Chem. 2001, 66, 6305. In the current work, we initially formed TFA salts of 17 and 19 prior to submission to the RCM conditions but subsequently found that the reactions of free amines 17 and 19 with ruthenium complex 11 gave similar results.
45. Cadot, C.; Dalko, P. I.; Cossy, J. Tetrahedron Lett. 2002, 43, 1839.
46. 3 overnight (see Supporting Information).