Transition metal-promoted three-component triene/alkyne cycloaddition. Facile construction of a novel polycyclic ring system

Journal of the American Chemical Society

Volumn 118, Issue 25, 1996, Pages 6094-6095

  Rigby, James H ^a   Warshakoon, Namal C ^a   Heeg, Mary Jane ^a  

^a WAYNE STATE UNIVERSITY   (United States)

Author keywords

[No Author keywords available]

Indexed keywords

POLYCYCLIC HYDROCARBON;

ARTICLE; CATALYSIS; DRUG SYNTHESIS; TECHNIQUE;

EID: 0030036494     PISSN: 00027863     EISSN: None     Source Type: Journal    
DOI: 10.1021/ja9609516     Document Type: Article

References (40)

1. For an excellent overview of the entire area of metal-mediated cycloaddition, see: Lautens, M.; Klute, W.; Tam, W. Chem. Rev. 1996, 96, 49.
2. Seven-membered ring synthesis: (a) Noyori, R. Acc. Chem. Res. 1979, 12, 61. (b) Hoffmann, H. M. R. Angew Chem., Int. Ed. Engl. 1984, 23, 1. (c) Trost, B. M.; MacPherson, D. T. J. Am. Chem. Soc. 1987, 109, 3483. (d) Wender, P. A.; Takahashi, H.; Witulski, B. J. Am. Chem. Soc. 1995, 117, 4720. (e) Schwiebert, K. E.; Stryker, J. M. J. Am. Chem. Soc. 1995, 117, 8275. Eight-membered ring synthesis: (f) Brenner, W.; Heimbach, P.; Hey, H.; Muller, E. W.; Wilke, G. Justus Uebigs Ann. Chem. 1969, 727, 161. (g) Diercks, R.; Stamp, L.; tom Dieck, H. Chem. Ber. 1984, 117, 1913. (h) Lautens. M.; Tam, W.; Sood, C. J. Org. Chem. 1993, 58, 4513. (i) Wender, P. A.; Ihle, N. C. J. Am. Chem. Soc. 1986, 108, 4678. (j) Davis, R. E.; Dodds, T. A.; Hseu, T.-H.; Wagnon, J. C.; Devon, T.; Tancrede, J.; McKennis, J. S.; Pettit, R. J. Am. Chem. Soc. 1974, 96, 7562. (k) Rigby, J. H.; Ateeq, H. S.; Charles, N. R.; Henshilwood, J. A.; Short, K. M.; Sugathapala, P. M. Tetrahedron 1993, 49, 5495. Nine-membered rings: (l) Kreiter, C. G.; Lehr, K.; Leyendecker, M.; Sheldrick, W. S.; Exner, R. Chem. Ber. 1991, 124, 3. Ten-membered rings: (m) Özkar, S.; Kurz, H.; Neugebauer, D.; Kreiter, C. G. J. Organomet. Chem. 1978, 160, 115. (n) Rigby, J. H.; Ateeq, H. S.; Charles, N. R.; Cuisiat, S. V.; Ferguson, M. D.; Henshilwood, J. A.; Krueger, A. C.; Ogbu, C. O.; Short, K. M.; Heeg, M. J. J. Am. Chem. Soc. 1993, 115, 1382.
3. Seven-membered ring synthesis: (a) Noyori, R. Acc. Chem. Res. 1979, 12, 61. (b) Hoffmann, H. M. R. Angew Chem., Int. Ed. Engl. 1984, 23, 1. (c) Trost, B. M.; MacPherson, D. T. J. Am. Chem. Soc. 1987, 109, 3483. (d) Wender, P. A.; Takahashi, H.; Witulski, B. J. Am. Chem. Soc. 1995, 117, 4720. (e) Schwiebert, K. E.; Stryker, J. M. J. Am. Chem. Soc. 1995, 117, 8275. Eight-membered ring synthesis: (f) Brenner, W.; Heimbach, P.; Hey, H.; Muller, E. W.; Wilke, G. Justus Uebigs Ann. Chem. 1969, 727, 161. (g) Diercks, R.; Stamp, L.; tom Dieck, H. Chem. Ber. 1984, 117, 1913. (h) Lautens. M.; Tam, W.; Sood, C. J. Org. Chem. 1993, 58, 4513. (i) Wender, P. A.; Ihle, N. C. J. Am. Chem. Soc. 1986, 108, 4678. (j) Davis, R. E.; Dodds, T. A.; Hseu, T.-H.; Wagnon, J. C.; Devon, T.; Tancrede, J.; McKennis, J. S.; Pettit, R. J. Am. Chem. Soc. 1974, 96, 7562. (k) Rigby, J. H.; Ateeq, H. S.; Charles, N. R.; Henshilwood, J. A.; Short, K. M.; Sugathapala, P. M. Tetrahedron 1993, 49, 5495. Nine-membered rings: (l) Kreiter, C. G.; Lehr, K.; Leyendecker, M.; Sheldrick, W. S.; Exner, R. Chem. Ber. 1991, 124, 3. Ten-membered rings: (m) Özkar, S.; Kurz, H.; Neugebauer, D.; Kreiter, C. G. J. Organomet. Chem. 1978, 160, 115. (n) Rigby, J. H.; Ateeq, H. S.; Charles, N. R.; Cuisiat, S. V.; Ferguson, M. D.; Henshilwood, J. A.; Krueger, A. C.; Ogbu, C. O.; Short, K. M.; Heeg, M. J. J. Am. Chem. Soc. 1993, 115, 1382.
4. Seven-membered ring synthesis: (a) Noyori, R. Acc. Chem. Res. 1979, 12, 61. (b) Hoffmann, H. M. R. Angew Chem., Int. Ed. Engl. 1984, 23, 1. (c) Trost, B. M.; MacPherson, D. T. J. Am. Chem. Soc. 1987, 109, 3483. (d) Wender, P. A.; Takahashi, H.; Witulski, B. J. Am. Chem. Soc. 1995, 117, 4720. (e) Schwiebert, K. E.; Stryker, J. M. J. Am. Chem. Soc. 1995, 117, 8275. Eight-membered ring synthesis: (f) Brenner, W.; Heimbach, P.; Hey, H.; Muller, E. W.; Wilke, G. Justus Uebigs Ann. Chem. 1969, 727, 161. (g) Diercks, R.; Stamp, L.; tom Dieck, H. Chem. Ber. 1984, 117, 1913. (h) Lautens. M.; Tam, W.; Sood, C. J. Org. Chem. 1993, 58, 4513. (i) Wender, P. A.; Ihle, N. C. J. Am. Chem. Soc. 1986, 108, 4678. (j) Davis, R. E.; Dodds, T. A.; Hseu, T.-H.; Wagnon, J. C.; Devon, T.; Tancrede, J.; McKennis, J. S.; Pettit, R. J. Am. Chem. Soc. 1974, 96, 7562. (k) Rigby, J. H.; Ateeq, H. S.; Charles, N. R.; Henshilwood, J. A.; Short, K. M.; Sugathapala, P. M. Tetrahedron 1993, 49, 5495. Nine-membered rings: (l) Kreiter, C. G.; Lehr, K.; Leyendecker, M.; Sheldrick, W. S.; Exner, R. Chem. Ber. 1991, 124, 3. Ten-membered rings: (m) Özkar, S.; Kurz, H.; Neugebauer, D.; Kreiter, C. G. J. Organomet. Chem. 1978, 160, 115. (n) Rigby, J. H.; Ateeq, H. S.; Charles, N. R.; Cuisiat, S. V.; Ferguson, M. D.; Henshilwood, J. A.; Krueger, A. C.; Ogbu, C. O.; Short, K. M.; Heeg, M. J. J. Am. Chem. Soc. 1993, 115, 1382.
5. Seven-membered ring synthesis: (a) Noyori, R. Acc. Chem. Res. 1979, 12, 61. (b) Hoffmann, H. M. R. Angew Chem., Int. Ed. Engl. 1984, 23, 1. (c) Trost, B. M.; MacPherson, D. T. J. Am. Chem. Soc. 1987, 109, 3483. (d) Wender, P. A.; Takahashi, H.; Witulski, B. J. Am. Chem. Soc. 1995, 117, 4720. (e) Schwiebert, K. E.; Stryker, J. M. J. Am. Chem. Soc. 1995, 117, 8275. Eight-membered ring synthesis: (f) Brenner, W.; Heimbach, P.; Hey, H.; Muller, E. W.; Wilke, G. Justus Uebigs Ann. Chem. 1969, 727, 161. (g) Diercks, R.; Stamp, L.; tom Dieck, H. Chem. Ber. 1984, 117, 1913. (h) Lautens. M.; Tam, W.; Sood, C. J. Org. Chem. 1993, 58, 4513. (i) Wender, P. A.; Ihle, N. C. J. Am. Chem. Soc. 1986, 108, 4678. (j) Davis, R. E.; Dodds, T. A.; Hseu, T.-H.; Wagnon, J. C.; Devon, T.; Tancrede, J.; McKennis, J. S.; Pettit, R. J. Am. Chem. Soc. 1974, 96, 7562. (k) Rigby, J. H.; Ateeq, H. S.; Charles, N. R.; Henshilwood, J. A.; Short, K. M.; Sugathapala, P. M. Tetrahedron 1993, 49, 5495. Nine-membered rings: (l) Kreiter, C. G.; Lehr, K.; Leyendecker, M.; Sheldrick, W. S.; Exner, R. Chem. Ber. 1991, 124, 3. Ten-membered rings: (m) Özkar, S.; Kurz, H.; Neugebauer, D.; Kreiter, C. G. J. Organomet. Chem. 1978, 160, 115. (n) Rigby, J. H.; Ateeq, H. S.; Charles, N. R.; Cuisiat, S. V.; Ferguson, M. D.; Henshilwood, J. A.; Krueger, A. C.; Ogbu, C. O.; Short, K. M.; Heeg, M. J. J. Am. Chem. Soc. 1993, 115, 1382.
6. Seven-membered ring synthesis: (a) Noyori, R. Acc. Chem. Res. 1979, 12, 61. (b) Hoffmann, H. M. R. Angew Chem., Int. Ed. Engl. 1984, 23, 1. (c) Trost, B. M.; MacPherson, D. T. J. Am. Chem. Soc. 1987, 109, 3483. (d) Wender, P. A.; Takahashi, H.; Witulski, B. J. Am. Chem. Soc. 1995, 117, 4720. (e) Schwiebert, K. E.; Stryker, J. M. J. Am. Chem. Soc. 1995, 117, 8275. Eight-membered ring synthesis: (f) Brenner, W.; Heimbach, P.; Hey, H.; Muller, E. W.; Wilke, G. Justus Uebigs Ann. Chem. 1969, 727, 161. (g) Diercks, R.; Stamp, L.; tom Dieck, H. Chem. Ber. 1984, 117, 1913. (h) Lautens. M.; Tam, W.; Sood, C. J. Org. Chem. 1993, 58, 4513. (i) Wender, P. A.; Ihle, N. C. J. Am. Chem. Soc. 1986, 108, 4678. (j) Davis, R. E.; Dodds, T. A.; Hseu, T.-H.; Wagnon, J. C.; Devon, T.; Tancrede, J.; McKennis, J. S.; Pettit, R. J. Am. Chem. Soc. 1974, 96, 7562. (k) Rigby, J. H.; Ateeq, H. S.; Charles, N. R.; Henshilwood, J. A.; Short, K. M.; Sugathapala, P. M. Tetrahedron 1993, 49, 5495. Nine-membered rings: (l) Kreiter, C. G.; Lehr, K.; Leyendecker, M.; Sheldrick, W. S.; Exner, R. Chem. Ber. 1991, 124, 3. Ten-membered rings: (m) Özkar, S.; Kurz, H.; Neugebauer, D.; Kreiter, C. G. J. Organomet. Chem. 1978, 160, 115. (n) Rigby, J. H.; Ateeq, H. S.; Charles, N. R.; Cuisiat, S. V.; Ferguson, M. D.; Henshilwood, J. A.; Krueger, A. C.; Ogbu, C. O.; Short, K. M.; Heeg, M. J. J. Am. Chem. Soc. 1993, 115, 1382.
7. Seven-membered ring synthesis: (a) Noyori, R. Acc. Chem. Res. 1979, 12, 61. (b) Hoffmann, H. M. R. Angew Chem., Int. Ed. Engl. 1984, 23, 1. (c) Trost, B. M.; MacPherson, D. T. J. Am. Chem. Soc. 1987, 109, 3483. (d) Wender, P. A.; Takahashi, H.; Witulski, B. J. Am. Chem. Soc. 1995, 117, 4720. (e) Schwiebert, K. E.; Stryker, J. M. J. Am. Chem. Soc. 1995, 117, 8275. Eight-membered ring synthesis: (f) Brenner, W.; Heimbach, P.; Hey, H.; Muller, E. W.; Wilke, G. Justus Uebigs Ann. Chem. 1969, 727, 161. (g) Diercks, R.; Stamp, L.; tom Dieck, H. Chem. Ber. 1984, 117, 1913. (h) Lautens. M.; Tam, W.; Sood, C. J. Org. Chem. 1993, 58, 4513. (i) Wender, P. A.; Ihle, N. C. J. Am. Chem. Soc. 1986, 108, 4678. (j) Davis, R. E.; Dodds, T. A.; Hseu, T.-H.; Wagnon, J. C.; Devon, T.; Tancrede, J.; McKennis, J. S.; Pettit, R. J. Am. Chem. Soc. 1974, 96, 7562. (k) Rigby, J. H.; Ateeq, H. S.; Charles, N. R.; Henshilwood, J. A.; Short, K. M.; Sugathapala, P. M. Tetrahedron 1993, 49, 5495. Nine-membered rings: (l) Kreiter, C. G.; Lehr, K.; Leyendecker, M.; Sheldrick, W. S.; Exner, R. Chem. Ber. 1991, 124, 3. Ten-membered rings: (m) Özkar, S.; Kurz, H.; Neugebauer, D.; Kreiter, C. G. J. Organomet. Chem. 1978, 160, 115. (n) Rigby, J. H.; Ateeq, H. S.; Charles, N. R.; Cuisiat, S. V.; Ferguson, M. D.; Henshilwood, J. A.; Krueger, A. C.; Ogbu, C. O.; Short, K. M.; Heeg, M. J. J. Am. Chem. Soc. 1993, 115, 1382.
8. Seven-membered ring synthesis: (a) Noyori, R. Acc. Chem. Res. 1979, 12, 61. (b) Hoffmann, H. M. R. Angew Chem., Int. Ed. Engl. 1984, 23, 1. (c) Trost, B. M.; MacPherson, D. T. J. Am. Chem. Soc. 1987, 109, 3483. (d) Wender, P. A.; Takahashi, H.; Witulski, B. J. Am. Chem. Soc. 1995, 117, 4720. (e) Schwiebert, K. E.; Stryker, J. M. J. Am. Chem. Soc. 1995, 117, 8275. Eight-membered ring synthesis: (f) Brenner, W.; Heimbach, P.; Hey, H.; Muller, E. W.; Wilke, G. Justus Uebigs Ann. Chem. 1969, 727, 161. (g) Diercks, R.; Stamp, L.; tom Dieck, H. Chem. Ber. 1984, 117, 1913. (h) Lautens. M.; Tam, W.; Sood, C. J. Org. Chem. 1993, 58, 4513. (i) Wender, P. A.; Ihle, N. C. J. Am. Chem. Soc. 1986, 108, 4678. (j) Davis, R. E.; Dodds, T. A.; Hseu, T.-H.; Wagnon, J. C.; Devon, T.; Tancrede, J.; McKennis, J. S.; Pettit, R. J. Am. Chem. Soc. 1974, 96, 7562. (k) Rigby, J. H.; Ateeq, H. S.; Charles, N. R.; Henshilwood, J. A.; Short, K. M.; Sugathapala, P. M. Tetrahedron 1993, 49, 5495. Nine-membered rings: (l) Kreiter, C. G.; Lehr, K.; Leyendecker, M.; Sheldrick, W. S.; Exner, R. Chem. Ber. 1991, 124, 3. Ten-membered rings: (m) Özkar, S.; Kurz, H.; Neugebauer, D.; Kreiter, C. G. J. Organomet. Chem. 1978, 160, 115. (n) Rigby, J. H.; Ateeq, H. S.; Charles, N. R.; Cuisiat, S. V.; Ferguson, M. D.; Henshilwood, J. A.; Krueger, A. C.; Ogbu, C. O.; Short, K. M.; Heeg, M. J. J. Am. Chem. Soc. 1993, 115, 1382.
9. Seven-membered ring synthesis: (a) Noyori, R. Acc. Chem. Res. 1979, 12, 61. (b) Hoffmann, H. M. R. Angew Chem., Int. Ed. Engl. 1984, 23, 1. (c) Trost, B. M.; MacPherson, D. T. J. Am. Chem. Soc. 1987, 109, 3483. (d) Wender, P. A.; Takahashi, H.; Witulski, B. J. Am. Chem. Soc. 1995, 117, 4720. (e) Schwiebert, K. E.; Stryker, J. M. J. Am. Chem. Soc. 1995, 117, 8275. Eight-membered ring synthesis: (f) Brenner, W.; Heimbach, P.; Hey, H.; Muller, E. W.; Wilke, G. Justus Uebigs Ann. Chem. 1969, 727, 161. (g) Diercks, R.; Stamp, L.; tom Dieck, H. Chem. Ber. 1984, 117, 1913. (h) Lautens. M.; Tam, W.; Sood, C. J. Org. Chem. 1993, 58, 4513. (i) Wender, P. A.; Ihle, N. C. J. Am. Chem. Soc. 1986, 108, 4678. (j) Davis, R. E.; Dodds, T. A.; Hseu, T.-H.; Wagnon, J. C.; Devon, T.; Tancrede, J.; McKennis, J. S.; Pettit, R. J. Am. Chem. Soc. 1974, 96, 7562. (k) Rigby, J. H.; Ateeq, H. S.; Charles, N. R.; Henshilwood, J. A.; Short, K. M.; Sugathapala, P. M. Tetrahedron 1993, 49, 5495. Nine-membered rings: (l) Kreiter, C. G.; Lehr, K.; Leyendecker, M.; Sheldrick, W. S.; Exner, R. Chem. Ber. 1991, 124, 3. Ten-membered rings: (m) Özkar, S.; Kurz, H.; Neugebauer, D.; Kreiter, C. G. J. Organomet. Chem. 1978, 160, 115. (n) Rigby, J. H.; Ateeq, H. S.; Charles, N. R.; Cuisiat, S. V.; Ferguson, M. D.; Henshilwood, J. A.; Krueger, A. C.; Ogbu, C. O.; Short, K. M.; Heeg, M. J. J. Am. Chem. Soc. 1993, 115, 1382.
10. Seven-membered ring synthesis: (a) Noyori, R. Acc. Chem. Res. 1979, 12, 61. (b) Hoffmann, H. M. R. Angew Chem., Int. Ed. Engl. 1984, 23, 1. (c) Trost, B. M.; MacPherson, D. T. J. Am. Chem. Soc. 1987, 109, 3483. (d) Wender, P. A.; Takahashi, H.; Witulski, B. J. Am. Chem. Soc. 1995, 117, 4720. (e) Schwiebert, K. E.; Stryker, J. M. J. Am. Chem. Soc. 1995, 117, 8275. Eight-membered ring synthesis: (f) Brenner, W.; Heimbach, P.; Hey, H.; Muller, E. W.; Wilke, G. Justus Uebigs Ann. Chem. 1969, 727, 161. (g) Diercks, R.; Stamp, L.; tom Dieck, H. Chem. Ber. 1984, 117, 1913. (h) Lautens. M.; Tam, W.; Sood, C. J. Org. Chem. 1993, 58, 4513. (i) Wender, P. A.; Ihle, N. C. J. Am. Chem. Soc. 1986, 108, 4678. (j) Davis, R. E.; Dodds, T. A.; Hseu, T.-H.; Wagnon, J. C.; Devon, T.; Tancrede, J.; McKennis, J. S.; Pettit, R. J. Am. Chem. Soc. 1974, 96, 7562. (k) Rigby, J. H.; Ateeq, H. S.; Charles, N. R.; Henshilwood, J. A.; Short, K. M.; Sugathapala, P. M. Tetrahedron 1993, 49, 5495. Nine-membered rings: (l) Kreiter, C. G.; Lehr, K.; Leyendecker, M.; Sheldrick, W. S.; Exner, R. Chem. Ber. 1991, 124, 3. Ten-membered rings: (m) Özkar, S.; Kurz, H.; Neugebauer, D.; Kreiter, C. G. J. Organomet. Chem. 1978, 160, 115. (n) Rigby, J. H.; Ateeq, H. S.; Charles, N. R.; Cuisiat, S. V.; Ferguson, M. D.; Henshilwood, J. A.; Krueger, A. C.; Ogbu, C. O.; Short, K. M.; Heeg, M. J. J. Am. Chem. Soc. 1993, 115, 1382.
11. Seven-membered ring synthesis: (a) Noyori, R. Acc. Chem. Res. 1979, 12, 61. (b) Hoffmann, H. M. R. Angew Chem., Int. Ed. Engl. 1984, 23, 1. (c) Trost, B. M.; MacPherson, D. T. J. Am. Chem. Soc. 1987, 109, 3483. (d) Wender, P. A.; Takahashi, H.; Witulski, B. J. Am. Chem. Soc. 1995, 117, 4720. (e) Schwiebert, K. E.; Stryker, J. M. J. Am. Chem. Soc. 1995, 117, 8275. Eight-membered ring synthesis: (f) Brenner, W.; Heimbach, P.; Hey, H.; Muller, E. W.; Wilke, G. Justus Uebigs Ann. Chem. 1969, 727, 161. (g) Diercks, R.; Stamp, L.; tom Dieck, H. Chem. Ber. 1984, 117, 1913. (h) Lautens. M.; Tam, W.; Sood, C. J. Org. Chem. 1993, 58, 4513. (i) Wender, P. A.; Ihle, N. C. J. Am. Chem. Soc. 1986, 108, 4678. (j) Davis, R. E.; Dodds, T. A.; Hseu, T.-H.; Wagnon, J. C.; Devon, T.; Tancrede, J.; McKennis, J. S.; Pettit, R. J. Am. Chem. Soc. 1974, 96, 7562. (k) Rigby, J. H.; Ateeq, H. S.; Charles, N. R.; Henshilwood, J. A.; Short, K. M.; Sugathapala, P. M. Tetrahedron 1993, 49, 5495. Nine-membered rings: (l) Kreiter, C. G.; Lehr, K.; Leyendecker, M.; Sheldrick, W. S.; Exner, R. Chem. Ber. 1991, 124, 3. Ten-membered rings: (m) Özkar, S.; Kurz, H.; Neugebauer, D.; Kreiter, C. G. J. Organomet. Chem. 1978, 160, 115. (n) Rigby, J. H.; Ateeq, H. S.; Charles, N. R.; Cuisiat, S. V.; Ferguson, M. D.; Henshilwood, J. A.; Krueger, A. C.; Ogbu, C. O.; Short, K. M.; Heeg, M. J. J. Am. Chem. Soc. 1993, 115, 1382.
12. Seven-membered ring synthesis: (a) Noyori, R. Acc. Chem. Res. 1979, 12, 61. (b) Hoffmann, H. M. R. Angew Chem., Int. Ed. Engl. 1984, 23, 1. (c) Trost, B. M.; MacPherson, D. T. J. Am. Chem. Soc. 1987, 109, 3483. (d) Wender, P. A.; Takahashi, H.; Witulski, B. J. Am. Chem. Soc. 1995, 117, 4720. (e) Schwiebert, K. E.; Stryker, J. M. J. Am. Chem. Soc. 1995, 117, 8275. Eight-membered ring synthesis: (f) Brenner, W.; Heimbach, P.; Hey, H.; Muller, E. W.; Wilke, G. Justus Uebigs Ann. Chem. 1969, 727, 161. (g) Diercks, R.; Stamp, L.; tom Dieck, H. Chem. Ber. 1984, 117, 1913. (h) Lautens. M.; Tam, W.; Sood, C. J. Org. Chem. 1993, 58, 4513. (i) Wender, P. A.; Ihle, N. C. J. Am. Chem. Soc. 1986, 108, 4678. (j) Davis, R. E.; Dodds, T. A.; Hseu, T.-H.; Wagnon, J. C.; Devon, T.; Tancrede, J.; McKennis, J. S.; Pettit, R. J. Am. Chem. Soc. 1974, 96, 7562. (k) Rigby, J. H.; Ateeq, H. S.; Charles, N. R.; Henshilwood, J. A.; Short, K. M.; Sugathapala, P. M. Tetrahedron 1993, 49, 5495. Nine-membered rings: (l) Kreiter, C. G.; Lehr, K.; Leyendecker, M.; Sheldrick, W. S.; Exner, R. Chem. Ber. 1991, 124, 3. Ten-membered rings: (m) Özkar, S.; Kurz, H.; Neugebauer, D.; Kreiter, C. G. J. Organomet. Chem. 1978, 160, 115. (n) Rigby, J. H.; Ateeq, H. S.; Charles, N. R.; Cuisiat, S. V.; Ferguson, M. D.; Henshilwood, J. A.; Krueger, A. C.; Ogbu, C. O.; Short, K. M.; Heeg, M. J. J. Am. Chem. Soc. 1993, 115, 1382.
13. Seven-membered ring synthesis: (a) Noyori, R. Acc. Chem. Res. 1979, 12, 61. (b) Hoffmann, H. M. R. Angew Chem., Int. Ed. Engl. 1984, 23, 1. (c) Trost, B. M.; MacPherson, D. T. J. Am. Chem. Soc. 1987, 109, 3483. (d) Wender, P. A.; Takahashi, H.; Witulski, B. J. Am. Chem. Soc. 1995, 117, 4720. (e) Schwiebert, K. E.; Stryker, J. M. J. Am. Chem. Soc. 1995, 117, 8275. Eight-membered ring synthesis: (f) Brenner, W.; Heimbach, P.; Hey, H.; Muller, E. W.; Wilke, G. Justus Uebigs Ann. Chem. 1969, 727, 161. (g) Diercks, R.; Stamp, L.; tom Dieck, H. Chem. Ber. 1984, 117, 1913. (h) Lautens. M.; Tam, W.; Sood, C. J. Org. Chem. 1993, 58, 4513. (i) Wender, P. A.; Ihle, N. C. J. Am. Chem. Soc. 1986, 108, 4678. (j) Davis, R. E.; Dodds, T. A.; Hseu, T.-H.; Wagnon, J. C.; Devon, T.; Tancrede, J.; McKennis, J. S.; Pettit, R. J. Am. Chem. Soc. 1974, 96, 7562. (k) Rigby, J. H.; Ateeq, H. S.; Charles, N. R.; Henshilwood, J. A.; Short, K. M.; Sugathapala, P. M. Tetrahedron 1993, 49, 5495. Nine-membered rings: (l) Kreiter, C. G.; Lehr, K.; Leyendecker, M.; Sheldrick, W. S.; Exner, R. Chem. Ber. 1991, 124, 3. Ten-membered rings: (m) Özkar, S.; Kurz, H.; Neugebauer, D.; Kreiter, C. G. J. Organomet. Chem. 1978, 160, 115. (n) Rigby, J. H.; Ateeq, H. S.; Charles, N. R.; Cuisiat, S. V.; Ferguson, M. D.; Henshilwood, J. A.; Krueger, A. C.; Ogbu, C. O.; Short, K. M.; Heeg, M. J. J. Am. Chem. Soc. 1993, 115, 1382.
14. Seven-membered ring synthesis: (a) Noyori, R. Acc. Chem. Res. 1979, 12, 61. (b) Hoffmann, H. M. R. Angew Chem., Int. Ed. Engl. 1984, 23, 1. (c) Trost, B. M.; MacPherson, D. T. J. Am. Chem. Soc. 1987, 109, 3483. (d) Wender, P. A.; Takahashi, H.; Witulski, B. J. Am. Chem. Soc. 1995, 117, 4720. (e) Schwiebert, K. E.; Stryker, J. M. J. Am. Chem. Soc. 1995, 117, 8275. Eight-membered ring synthesis: (f) Brenner, W.; Heimbach, P.; Hey, H.; Muller, E. W.; Wilke, G. Justus Uebigs Ann. Chem. 1969, 727, 161. (g) Diercks, R.; Stamp, L.; tom Dieck, H. Chem. Ber. 1984, 117, 1913. (h) Lautens. M.; Tam, W.; Sood, C. J. Org. Chem. 1993, 58, 4513. (i) Wender, P. A.; Ihle, N. C. J. Am. Chem. Soc. 1986, 108, 4678. (j) Davis, R. E.; Dodds, T. A.; Hseu, T.-H.; Wagnon, J. C.; Devon, T.; Tancrede, J.; McKennis, J. S.; Pettit, R. J. Am. Chem. Soc. 1974, 96, 7562. (k) Rigby, J. H.; Ateeq, H. S.; Charles, N. R.; Henshilwood, J. A.; Short, K. M.; Sugathapala, P. M. Tetrahedron 1993, 49, 5495. Nine-membered rings: (l) Kreiter, C. G.; Lehr, K.; Leyendecker, M.; Sheldrick, W. S.; Exner, R. Chem. Ber. 1991, 124, 3. Ten-membered rings: (m) Özkar, S.; Kurz, H.; Neugebauer, D.; Kreiter, C. G. J. Organomet. Chem. 1978, 160, 115. (n) Rigby, J. H.; Ateeq, H. S.; Charles, N. R.; Cuisiat, S. V.; Ferguson, M. D.; Henshilwood, J. A.; Krueger, A. C.; Ogbu, C. O.; Short, K. M.; Heeg, M. J. J. Am. Chem. Soc. 1993, 115, 1382.
15. Seven-membered ring synthesis: (a) Noyori, R. Acc. Chem. Res. 1979, 12, 61. (b) Hoffmann, H. M. R. Angew Chem., Int. Ed. Engl. 1984, 23, 1. (c) Trost, B. M.; MacPherson, D. T. J. Am. Chem. Soc. 1987, 109, 3483. (d) Wender, P. A.; Takahashi, H.; Witulski, B. J. Am. Chem. Soc. 1995, 117, 4720. (e) Schwiebert, K. E.; Stryker, J. M. J. Am. Chem. Soc. 1995, 117, 8275. Eight-membered ring synthesis: (f) Brenner, W.; Heimbach, P.; Hey, H.; Muller, E. W.; Wilke, G. Justus Uebigs Ann. Chem. 1969, 727, 161. (g) Diercks, R.; Stamp, L.; tom Dieck, H. Chem. Ber. 1984, 117, 1913. (h) Lautens. M.; Tam, W.; Sood, C. J. Org. Chem. 1993, 58, 4513. (i) Wender, P. A.; Ihle, N. C. J. Am. Chem. Soc. 1986, 108, 4678. (j) Davis, R. E.; Dodds, T. A.; Hseu, T.-H.; Wagnon, J. C.; Devon, T.; Tancrede, J.; McKennis, J. S.; Pettit, R. J. Am. Chem. Soc. 1974, 96, 7562. (k) Rigby, J. H.; Ateeq, H. S.; Charles, N. R.; Henshilwood, J. A.; Short, K. M.; Sugathapala, P. M. Tetrahedron 1993, 49, 5495. Nine-membered rings: (l) Kreiter, C. G.; Lehr, K.; Leyendecker, M.; Sheldrick, W. S.; Exner, R. Chem. Ber. 1991, 124, 3. Ten-membered rings: (m) Özkar, S.; Kurz, H.; Neugebauer, D.; Kreiter, C. G. J. Organomet. Chem. 1978, 160, 115. (n) Rigby, J. H.; Ateeq, H. S.; Charles, N. R.; Cuisiat, S. V.; Ferguson, M. D.; Henshilwood, J. A.; Krueger, A. C.; Ogbu, C. O.; Short, K. M.; Heeg, M. J. J. Am. Chem. Soc. 1993, 115, 1382.
16. (a) Vollhardt, K. P. C. Angew Chem., Int. Ed. Engl. 1984, 23, 539.
17. (b) Sato, Y.; Nishimata, T.; Mori, M. J. Org. Chem. 1994, 59, 6133.
18. (c) Neidlein, R.; Kux, U. Helv. Chim. Acta. 1994, 77, 1051.
19. (d) Negishi, E.; Harring, L. S.; Owczarczyk, Z.; Mohamud, M. M.; Ay, M. Tetrahedron Lett. 1992, 33, 3253.
20. Lautens, M.; Tam, W.; Lautens, J. C.; Edwards, L. G.; Crudden, C. M.; Smith, A. C. J. Am. Chem. Soc. 1995, 117, 6863 and references cited therein.
21. (a) Wilson, A. M.; Waldman, T. E.; Rheingold, A. L.; Ernst, R. D. J. Am. Chem. Soc. 1992, 114, 6252.
22. (b) Wang, C.; Sheridan, J. B.; Chung, H.-J.; Coté, M. L.; Lalancette, R. A.; Rheingold, A. L. J. Am. Chem. Soc. 1994, 116, 8966.
23. (c) Herndon, J. W.; Zora, M.; Patel, P. P. Chatterjee, G.; Matasi, J. J.; Tumer, S. U. Tetrahedron 1993, 49, 5507.
24. (d) Grevels. F.-W.; Schnieder, K. Angew. Chem., Int. Ed. Engl. 1981, 20, 410.
25. A similar ring system has been prepared previously in an Fe(0)-mediated process: Goddard, R.; Woodward, P. J. Chem. Soc., Dalton Trans. 1979,711.
26. Rigby, J. H.; Ateeq, H. S.; Krueger, A. C. Tetrahedron Lett. 1992, 33, 5873.
27. 13C NMR, IR) and analytical (combustion analysis and/or HRMS) data consistent with the assigned structure.
28. The structure of this compound was determined by single-crystal X-ray analysis.
29. (a) Chaffee, K.; Huo, P.; Sheridan, J. B.; Barbieri, A.; Aistars, A.; Lalancette, R. A.; Ostrander, R. L.; Rheingold, A. L. J. Am. Chem. Soc. 1995, 117, 1900.
30. (b) Brammer, L.; Dunne, B. J.; Green, M.; Moran, G.; Orpen, A. G.; Reeve, C.; Schaverien, C. J. J. Chem. Soc., Dalton Trans. 1993, 1747.
31. (c) Klein, R.; Sedmera, P.; Cejka, J.; Mach, K. J. Organomet. Chem. 1992, 436, 143.
32. (d) Chaffee, K.; Sheridan, J. B.; Aistars, A. Organometallics 1992, 11, 18.
33. (e) Fischler, I.; Grevels, F.-W.; Leitich, J.; Özkar, S. Chem. Ber. 1991, 124, 2857.
34. (f) Mach, K.; Antropiusová, H.; Petrusová, L.; Hanuš;, V.; Tetrahedron, F. Tetrahedron 1984, 40, 3295.
35. (g) Nagashima, H.; Matsuda, H.; Itoh, K. J. Organomet. Chem. 1983, 258, C15.
36. Efforts to arrest the current reaction at the 1:1 adduct stage by employing 1 equiv of alkyne were only partially successful (see ref 14).
37. Rigby, J. H.; Sugathapala, P.; Heeg, M. J. J Am. Chem. Soc. 1995, 117, 8851.
38. Rigby, J. H.; Short, K. M.; Ateeq, H. S.; Henshilwood, J. A. J. Org. Chem. 1992, 57, 5290.
39. Complex 8 was prepared by reacting complex 1 with 0.1 equiv of trimethylsilylacetylene under standard photochemical conditions. Excess 1 was removed chromatographically to afford crude 8 in low yield.
40. This observation suggests that two different alkyne partners could be reacted sequentially on a preparative scale if the rapid second addition could be slowed sufficiently. Work on this intriguing possibility is currently underway.