Multicomponent cycloadditions: The four-component [5+1+2+1] cycloaddition of vinylcyclopropanes, alkynes, and CO

Journal of the American Chemical Society

Volumn 127, Issue 9, 2005, Pages 2836-2837

  Wender, Paul A ^a   Gamber, Gabriel G ^a   Hubbard, Robert D ^a   Pham, Son M ^a   Zhang, Lei ^a  

^a STANFORD UNIVERSITY   (United States)

Author keywords

[No Author keywords available]

Indexed keywords

ALKYNE; CYCLOPROPANE;

ARTICLE; CHEMICAL REACTION; CYCLOADDITION; ELIMINATION REACTION; REACTION ANALYSIS; SUBSTITUTION REACTION; SYNTHESIS; X RAY CRYSTALLOGRAPHY;

EID: 14844290896     PISSN: 00027863     EISSN: None     Source Type: Journal    
DOI: 10.1021/ja042728b     Document Type: Article

References (62)

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4. For recent reviews of our work, see: (a) Wender, P. A.; Bi, F. C.; Gamber, G. G.; Gosselin, F.; Hubbard, R. D.; Scanio, M. J. C.; Sun, R.; Williams, T. J.; Zhang, L. Pure Appl. Chem. 2002, 74, 25. (b) Wender, P. A.; Baryza, J. L.; Brenner, S. E.; Clarke, M. O.; Gamber, G. G.; Horan, J. C.; Jessop, T. C.; Kan, C.; Pattabiraman, K.; Williams, T. J. Pure Appl. Chem. 2003, 75, 143.
5. For recent reviews of our work, see: (a) Wender, P. A.; Bi, F. C.; Gamber, G. G.; Gosselin, F.; Hubbard, R. D.; Scanio, M. J. C.; Sun, R.; Williams, T. J.; Zhang, L. Pure Appl. Chem. 2002, 74, 25. (b) Wender, P. A.; Baryza, J. L.; Brenner, S. E.; Clarke, M. O.; Gamber, G. G.; Horan, J. C.; Jessop, T. C.; Kan, C.; Pattabiraman, K.; Williams, T. J. Pure Appl. Chem. 2003, 75, 143.
6. For recent reviews of multicomponent reactions: (a) Dömling, A.; Ugi, I. Angew. Chem., Int. Ed. 2000, 39, 3168. (b) Tietze, L. F.; Modi, A. Med. Res. Rev. 2000, 20, 304. (c) Zhu, J. Eur. J. Org. Chem. 2003, 1133. (d) Orru, R. V. A.; de Greef, M. Synthesis 2003, 1471. (e) Bienaymé, H.; Hulme, C.; Oddon, G.; Schmitt, P. Chem. Eur. J. 2000, 6, 3321. For recent examples of multicomponent cycloadditions, see ref 8 and: f) Gilbertson, S. R.; DeBoef, B. J. Am. Chem. Soc. 2002, 124, 8784. (g) Evans, P. A.; Robinson, J. E.; Baum, E. W.; Fazal, A. N. J. Am. Chem. Soc 2002, 124, 8782. (h) Murakami, M.; Itami, K.; Ito, Y. Angew. Chem., Intl. Ed. 1998, 37, 3418. (i) Dzwiniel, T. L.; Etkin, N.; Stryker, J. M. J. Am. Chem. Soc. 1999, 121, 10640. (j) Ni, Y.; Montgomery, J. J. Am. Chem. Soc. 2004, 43, 11162. (k) Wender, P. A.; Gamber, G. G.; Hubbard, R. D.; Zhang, L. J. Am. Chem. Soc. 2002, 124, 2876. (l) Wender, P. A.; Deschamps, N. M.; Gamber, G. G. Angew. Chem., Int. Ed. 2003, 42, 1853. (m) Wender, P. A.; Croatt, M. P.; Deschamps, N. M. J. Am. Chem. Soc. 2004, 126, 5948. (n) Wender, P. A.; Deschamps, N. M.; Williams, T. J. Angew. Chem., Int. Ed. 2004, 43, 3076.
7. For recent reviews of multicomponent reactions: (a) Dömling, A.; Ugi, I. Angew. Chem., Int. Ed. 2000, 39, 3168. (b) Tietze, L. F.; Modi, A. Med. Res. Rev. 2000, 20, 304. (c) Zhu, J. Eur. J. Org. Chem. 2003, 1133. (d) Orru, R. V. A.; de Greef, M. Synthesis 2003, 1471. (e) Bienaymé, H.; Hulme, C.; Oddon, G.; Schmitt, P. Chem. Eur. J. 2000, 6, 3321. For recent examples of multicomponent cycloadditions, see ref 8 and: f) Gilbertson, S. R.; DeBoef, B. J. Am. Chem. Soc. 2002, 124, 8784. (g) Evans, P. A.; Robinson, J. E.; Baum, E. W.; Fazal, A. N. J. Am. Chem. Soc 2002, 124, 8782. (h) Murakami, M.; Itami, K.; Ito, Y. Angew. Chem., Intl. Ed. 1998, 37, 3418. (i) Dzwiniel, T. L.; Etkin, N.; Stryker, J. M. J. Am. Chem. Soc. 1999, 121, 10640. (j) Ni, Y.; Montgomery, J. J. Am. Chem. Soc. 2004, 43, 11162. (k) Wender, P. A.; Gamber, G. G.; Hubbard, R. D.; Zhang, L. J. Am. Chem. Soc. 2002, 124, 2876. (l) Wender, P. A.; Deschamps, N. M.; Gamber, G. G. Angew. Chem., Int. Ed. 2003, 42, 1853. (m) Wender, P. A.; Croatt, M. P.; Deschamps, N. M. J. Am. Chem. Soc. 2004, 126, 5948. (n) Wender, P. A.; Deschamps, N. M.; Williams, T. J. Angew. Chem., Int. Ed. 2004, 43, 3076.
8. For recent reviews of multicomponent reactions: (a) Dömling, A.; Ugi, I. Angew. Chem., Int. Ed. 2000, 39, 3168. (b) Tietze, L. F.; Modi, A. Med. Res. Rev. 2000, 20, 304. (c) Zhu, J. Eur. J. Org. Chem. 2003, 1133. (d) Orru, R. V. A.; de Greef, M. Synthesis 2003, 1471. (e) Bienaymé, H.; Hulme, C.; Oddon, G.; Schmitt, P. Chem. Eur. J. 2000, 6, 3321. For recent examples of multicomponent cycloadditions, see ref 8 and: f) Gilbertson, S. R.; DeBoef, B. J. Am. Chem. Soc. 2002, 124, 8784. (g) Evans, P. A.; Robinson, J. E.; Baum, E. W.; Fazal, A. N. J. Am. Chem. Soc 2002, 124, 8782. (h) Murakami, M.; Itami, K.; Ito, Y. Angew. Chem., Intl. Ed. 1998, 37, 3418. (i) Dzwiniel, T. L.; Etkin, N.; Stryker, J. M. J. Am. Chem. Soc. 1999, 121, 10640. (j) Ni, Y.; Montgomery, J. J. Am. Chem. Soc. 2004, 43, 11162. (k) Wender, P. A.; Gamber, G. G.; Hubbard, R. D.; Zhang, L. J. Am. Chem. Soc. 2002, 124, 2876. (l) Wender, P. A.; Deschamps, N. M.; Gamber, G. G. Angew. Chem., Int. Ed. 2003, 42, 1853. (m) Wender, P. A.; Croatt, M. P.; Deschamps, N. M. J. Am. Chem. Soc. 2004, 126, 5948. (n) Wender, P. A.; Deschamps, N. M.; Williams, T. J. Angew. Chem., Int. Ed. 2004, 43, 3076.
9. For recent reviews of multicomponent reactions: (a) Dömling, A.; Ugi, I. Angew. Chem., Int. Ed. 2000, 39, 3168. (b) Tietze, L. F.; Modi, A. Med. Res. Rev. 2000, 20, 304. (c) Zhu, J. Eur. J. Org. Chem. 2003, 1133. (d) Orru, R. V. A.; de Greef, M. Synthesis 2003, 1471. (e) Bienaymé, H.; Hulme, C.; Oddon, G.; Schmitt, P. Chem. Eur. J. 2000, 6, 3321. For recent examples of multicomponent cycloadditions, see ref 8 and: f) Gilbertson, S. R.; DeBoef, B. J. Am. Chem. Soc. 2002, 124, 8784. (g) Evans, P. A.; Robinson, J. E.; Baum, E. W.; Fazal, A. N. J. Am. Chem. Soc 2002, 124, 8782. (h) Murakami, M.; Itami, K.; Ito, Y. Angew. Chem., Intl. Ed. 1998, 37, 3418. (i) Dzwiniel, T. L.; Etkin, N.; Stryker, J. M. J. Am. Chem. Soc. 1999, 121, 10640. (j) Ni, Y.; Montgomery, J. J. Am. Chem. Soc. 2004, 43, 11162. (k) Wender, P. A.; Gamber, G. G.; Hubbard, R. D.; Zhang, L. J. Am. Chem. Soc. 2002, 124, 2876. (l) Wender, P. A.; Deschamps, N. M.; Gamber, G. G. Angew. Chem., Int. Ed. 2003, 42, 1853. (m) Wender, P. A.; Croatt, M. P.; Deschamps, N. M. J. Am. Chem. Soc. 2004, 126, 5948. (n) Wender, P. A.; Deschamps, N. M.; Williams, T. J. Angew. Chem., Int. Ed. 2004, 43, 3076.
10. For recent reviews of multicomponent reactions: (a) Dömling, A.; Ugi, I. Angew. Chem., Int. Ed. 2000, 39, 3168. (b) Tietze, L. F.; Modi, A. Med. Res. Rev. 2000, 20, 304. (c) Zhu, J. Eur. J. Org. Chem. 2003, 1133. (d) Orru, R. V. A.; de Greef, M. Synthesis 2003, 1471. (e) Bienaymé, H.; Hulme, C.; Oddon, G.; Schmitt, P. Chem. Eur. J. 2000, 6, 3321. For recent examples of multicomponent cycloadditions, see ref 8 and: f) Gilbertson, S. R.; DeBoef, B. J. Am. Chem. Soc. 2002, 124, 8784. (g) Evans, P. A.; Robinson, J. E.; Baum, E. W.; Fazal, A. N. J. Am. Chem. Soc 2002, 124, 8782. (h) Murakami, M.; Itami, K.; Ito, Y. Angew. Chem., Intl. Ed. 1998, 37, 3418. (i) Dzwiniel, T. L.; Etkin, N.; Stryker, J. M. J. Am. Chem. Soc. 1999, 121, 10640. (j) Ni, Y.; Montgomery, J. J. Am. Chem. Soc. 2004, 43, 11162. (k) Wender, P. A.; Gamber, G. G.; Hubbard, R. D.; Zhang, L. J. Am. Chem. Soc. 2002, 124, 2876. (l) Wender, P. A.; Deschamps, N. M.; Gamber, G. G. Angew. Chem., Int. Ed. 2003, 42, 1853. (m) Wender, P. A.; Croatt, M. P.; Deschamps, N. M. J. Am. Chem. Soc. 2004, 126, 5948. (n) Wender, P. A.; Deschamps, N. M.; Williams, T. J. Angew. Chem., Int. Ed. 2004, 43, 3076.
11. For recent reviews of multicomponent reactions: (a) Dömling, A.; Ugi, I. Angew. Chem., Int. Ed. 2000, 39, 3168. (b) Tietze, L. F.; Modi, A. Med. Res. Rev. 2000, 20, 304. (c) Zhu, J. Eur. J. Org. Chem. 2003, 1133. (d) Orru, R. V. A.; de Greef, M. Synthesis 2003, 1471. (e) Bienaymé, H.; Hulme, C.; Oddon, G.; Schmitt, P. Chem. Eur. J. 2000, 6, 3321. For recent examples of multicomponent cycloadditions, see ref 8 and: f) Gilbertson, S. R.; DeBoef, B. J. Am. Chem. Soc. 2002, 124, 8784. (g) Evans, P. A.; Robinson, J. E.; Baum, E. W.; Fazal, A. N. J. Am. Chem. Soc 2002, 124, 8782. (h) Murakami, M.; Itami, K.; Ito, Y. Angew. Chem., Intl. Ed. 1998, 37, 3418. (i) Dzwiniel, T. L.; Etkin, N.; Stryker, J. M. J. Am. Chem. Soc. 1999, 121, 10640. (j) Ni, Y.; Montgomery, J. J. Am. Chem. Soc. 2004, 43, 11162. (k) Wender, P. A.; Gamber, G. G.; Hubbard, R. D.; Zhang, L. J. Am. Chem. Soc. 2002, 124, 2876. (l) Wender, P. A.; Deschamps, N. M.; Gamber, G. G. Angew. Chem., Int. Ed. 2003, 42, 1853. (m) Wender, P. A.; Croatt, M. P.; Deschamps, N. M. J. Am. Chem. Soc. 2004, 126, 5948. (n) Wender, P. A.; Deschamps, N. M.; Williams, T. J. Angew. Chem., Int. Ed. 2004, 43, 3076.
12. For recent reviews of multicomponent reactions: (a) Dömling, A.; Ugi, I. Angew. Chem., Int. Ed. 2000, 39, 3168. (b) Tietze, L. F.; Modi, A. Med. Res. Rev. 2000, 20, 304. (c) Zhu, J. Eur. J. Org. Chem. 2003, 1133. (d) Orru, R. V. A.; de Greef, M. Synthesis 2003, 1471. (e) Bienaymé, H.; Hulme, C.; Oddon, G.; Schmitt, P. Chem. Eur. J. 2000, 6, 3321. For recent examples of multicomponent cycloadditions, see ref 8 and: f) Gilbertson, S. R.; DeBoef, B. J. Am. Chem. Soc. 2002, 124, 8784. (g) Evans, P. A.; Robinson, J. E.; Baum, E. W.; Fazal, A. N. J. Am. Chem. Soc 2002, 124, 8782. (h) Murakami, M.; Itami, K.; Ito, Y. Angew. Chem., Intl. Ed. 1998, 37, 3418. (i) Dzwiniel, T. L.; Etkin, N.; Stryker, J. M. J. Am. Chem. Soc. 1999, 121, 10640. (j) Ni, Y.; Montgomery, J. J. Am. Chem. Soc. 2004, 43, 11162. (k) Wender, P. A.; Gamber, G. G.; Hubbard, R. D.; Zhang, L. J. Am. Chem. Soc. 2002, 124, 2876. (l) Wender, P. A.; Deschamps, N. M.; Gamber, G. G. Angew. Chem., Int. Ed. 2003, 42, 1853. (m) Wender, P. A.; Croatt, M. P.; Deschamps, N. M. J. Am. Chem. Soc. 2004, 126, 5948. (n) Wender, P. A.; Deschamps, N. M.; Williams, T. J. Angew. Chem., Int. Ed. 2004, 43, 3076.
13. For recent reviews of multicomponent reactions: (a) Dömling, A.; Ugi, I. Angew. Chem., Int. Ed. 2000, 39, 3168. (b) Tietze, L. F.; Modi, A. Med. Res. Rev. 2000, 20, 304. (c) Zhu, J. Eur. J. Org. Chem. 2003, 1133. (d) Orru, R. V. A.; de Greef, M. Synthesis 2003, 1471. (e) Bienaymé, H.; Hulme, C.; Oddon, G.; Schmitt, P. Chem. Eur. J. 2000, 6, 3321. For recent examples of multicomponent cycloadditions, see ref 8 and: f) Gilbertson, S. R.; DeBoef, B. J. Am. Chem. Soc. 2002, 124, 8784. (g) Evans, P. A.; Robinson, J. E.; Baum, E. W.; Fazal, A. N. J. Am. Chem. Soc 2002, 124, 8782. (h) Murakami, M.; Itami, K.; Ito, Y. Angew. Chem., Intl. Ed. 1998, 37, 3418. (i) Dzwiniel, T. L.; Etkin, N.; Stryker, J. M. J. Am. Chem. Soc. 1999, 121, 10640. (j) Ni, Y.; Montgomery, J. J. Am. Chem. Soc. 2004, 43, 11162. (k) Wender, P. A.; Gamber, G. G.; Hubbard, R. D.; Zhang, L. J. Am. Chem. Soc. 2002, 124, 2876. (l) Wender, P. A.; Deschamps, N. M.; Gamber, G. G. Angew. Chem., Int. Ed. 2003, 42, 1853. (m) Wender, P. A.; Croatt, M. P.; Deschamps, N. M. J. Am. Chem. Soc. 2004, 126, 5948. (n) Wender, P. A.; Deschamps, N. M.; Williams, T. J. Angew. Chem., Int. Ed. 2004, 43, 3076.
14. For recent reviews of multicomponent reactions: (a) Dömling, A.; Ugi, I. Angew. Chem., Int. Ed. 2000, 39, 3168. (b) Tietze, L. F.; Modi, A. Med. Res. Rev. 2000, 20, 304. (c) Zhu, J. Eur. J. Org. Chem. 2003, 1133. (d) Orru, R. V. A.; de Greef, M. Synthesis 2003, 1471. (e) Bienaymé, H.; Hulme, C.; Oddon, G.; Schmitt, P. Chem. Eur. J. 2000, 6, 3321. For recent examples of multicomponent cycloadditions, see ref 8 and: f) Gilbertson, S. R.; DeBoef, B. J. Am. Chem. Soc. 2002, 124, 8784. (g) Evans, P. A.; Robinson, J. E.; Baum, E. W.; Fazal, A. N. J. Am. Chem. Soc 2002, 124, 8782. (h) Murakami, M.; Itami, K.; Ito, Y. Angew. Chem., Intl. Ed. 1998, 37, 3418. (i) Dzwiniel, T. L.; Etkin, N.; Stryker, J. M. J. Am. Chem. Soc. 1999, 121, 10640. (j) Ni, Y.; Montgomery, J. J. Am. Chem. Soc. 2004, 43, 11162. (k) Wender, P. A.; Gamber, G. G.; Hubbard, R. D.; Zhang, L. J. Am. Chem. Soc. 2002, 124, 2876. (l) Wender, P. A.; Deschamps, N. M.; Gamber, G. G. Angew. Chem., Int. Ed. 2003, 42, 1853. (m) Wender, P. A.; Croatt, M. P.; Deschamps, N. M. J. Am. Chem. Soc. 2004, 126, 5948. (n) Wender, P. A.; Deschamps, N. M.; Williams, T. J. Angew. Chem., Int. Ed. 2004, 43, 3076.
15. For recent reviews of multicomponent reactions: (a) Dömling, A.; Ugi, I. Angew. Chem., Int. Ed. 2000, 39, 3168. (b) Tietze, L. F.; Modi, A. Med. Res. Rev. 2000, 20, 304. (c) Zhu, J. Eur. J. Org. Chem. 2003, 1133. (d) Orru, R. V. A.; de Greef, M. Synthesis 2003, 1471. (e) Bienaymé, H.; Hulme, C.; Oddon, G.; Schmitt, P. Chem. Eur. J. 2000, 6, 3321. For recent examples of multicomponent cycloadditions, see ref 8 and: f) Gilbertson, S. R.; DeBoef, B. J. Am. Chem. Soc. 2002, 124, 8784. (g) Evans, P. A.; Robinson, J. E.; Baum, E. W.; Fazal, A. N. J. Am. Chem. Soc 2002, 124, 8782. (h) Murakami, M.; Itami, K.; Ito, Y. Angew. Chem., Intl. Ed. 1998, 37, 3418. (i) Dzwiniel, T. L.; Etkin, N.; Stryker, J. M. J. Am. Chem. Soc. 1999, 121, 10640. (j) Ni, Y.; Montgomery, J. J. Am. Chem. Soc. 2004, 43, 11162. (k) Wender, P. A.; Gamber, G. G.; Hubbard, R. D.; Zhang, L. J. Am. Chem. Soc. 2002, 124, 2876. (l) Wender, P. A.; Deschamps, N. M.; Gamber, G. G. Angew. Chem., Int. Ed. 2003, 42, 1853. (m) Wender, P. A.; Croatt, M. P.; Deschamps, N. M. J. Am. Chem. Soc. 2004, 126, 5948. (n) Wender, P. A.; Deschamps, N. M.; Williams, T. J. Angew. Chem., Int. Ed. 2004, 43, 3076.
16. For recent reviews of multicomponent reactions: (a) Dömling, A.; Ugi, I. Angew. Chem., Int. Ed. 2000, 39, 3168. (b) Tietze, L. F.; Modi, A. Med. Res. Rev. 2000, 20, 304. (c) Zhu, J. Eur. J. Org. Chem. 2003, 1133. (d) Orru, R. V. A.; de Greef, M. Synthesis 2003, 1471. (e) Bienaymé, H.; Hulme, C.; Oddon, G.; Schmitt, P. Chem. Eur. J. 2000, 6, 3321. For recent examples of multicomponent cycloadditions, see ref 8 and: f) Gilbertson, S. R.; DeBoef, B. J. Am. Chem. Soc. 2002, 124, 8784. (g) Evans, P. A.; Robinson, J. E.; Baum, E. W.; Fazal, A. N. J. Am. Chem. Soc 2002, 124, 8782. (h) Murakami, M.; Itami, K.; Ito, Y. Angew. Chem., Intl. Ed. 1998, 37, 3418. (i) Dzwiniel, T. L.; Etkin, N.; Stryker, J. M. J. Am. Chem. Soc. 1999, 121, 10640. (j) Ni, Y.; Montgomery, J. J. Am. Chem. Soc. 2004, 43, 11162. (k) Wender, P. A.; Gamber, G. G.; Hubbard, R. D.; Zhang, L. J. Am. Chem. Soc. 2002, 124, 2876. (l) Wender, P. A.; Deschamps, N. M.; Gamber, G. G. Angew. Chem., Int. Ed. 2003, 42, 1853. (m) Wender, P. A.; Croatt, M. P.; Deschamps, N. M. J. Am. Chem. Soc. 2004, 126, 5948. (n) Wender, P. A.; Deschamps, N. M.; Williams, T. J. Angew. Chem., Int. Ed. 2004, 43, 3076.
17. For recent reviews of multicomponent reactions: (a) Dömling, A.; Ugi, I. Angew. Chem., Int. Ed. 2000, 39, 3168. (b) Tietze, L. F.; Modi, A. Med. Res. Rev. 2000, 20, 304. (c) Zhu, J. Eur. J. Org. Chem. 2003, 1133. (d) Orru, R. V. A.; de Greef, M. Synthesis 2003, 1471. (e) Bienaymé, H.; Hulme, C.; Oddon, G.; Schmitt, P. Chem. Eur. J. 2000, 6, 3321. For recent examples of multicomponent cycloadditions, see ref 8 and: f) Gilbertson, S. R.; DeBoef, B. J. Am. Chem. Soc. 2002, 124, 8784. (g) Evans, P. A.; Robinson, J. E.; Baum, E. W.; Fazal, A. N. J. Am. Chem. Soc 2002, 124, 8782. (h) Murakami, M.; Itami, K.; Ito, Y. Angew. Chem., Intl. Ed. 1998, 37, 3418. (i) Dzwiniel, T. L.; Etkin, N.; Stryker, J. M. J. Am. Chem. Soc. 1999, 121, 10640. (j) Ni, Y.; Montgomery, J. J. Am. Chem. Soc. 2004, 43, 11162. (k) Wender, P. A.; Gamber, G. G.; Hubbard, R. D.; Zhang, L. J. Am. Chem. Soc. 2002, 124, 2876. (l) Wender, P. A.; Deschamps, N. M.; Gamber, G. G. Angew. Chem., Int. Ed. 2003, 42, 1853. (m) Wender, P. A.; Croatt, M. P.; Deschamps, N. M. J. Am. Chem. Soc. 2004, 126, 5948. (n) Wender, P. A.; Deschamps, N. M.; Williams, T. J. Angew. Chem., Int. Ed. 2004, 43, 3076.
18. For recent reviews of multicomponent reactions: (a) Dömling, A.; Ugi, I. Angew. Chem., Int. Ed. 2000, 39, 3168. (b) Tietze, L. F.; Modi, A. Med. Res. Rev. 2000, 20, 304. (c) Zhu, J. Eur. J. Org. Chem. 2003, 1133. (d) Orru, R. V. A.; de Greef, M. Synthesis 2003, 1471. (e) Bienaymé, H.; Hulme, C.; Oddon, G.; Schmitt, P. Chem. Eur. J. 2000, 6, 3321. For recent examples of multicomponent cycloadditions, see ref 8 and: f) Gilbertson, S. R.; DeBoef, B. J. Am. Chem. Soc. 2002, 124, 8784. (g) Evans, P. A.; Robinson, J. E.; Baum, E. W.; Fazal, A. N. J. Am. Chem. Soc 2002, 124, 8782. (h) Murakami, M.; Itami, K.; Ito, Y. Angew. Chem., Intl. Ed. 1998, 37, 3418. (i) Dzwiniel, T. L.; Etkin, N.; Stryker, J. M. J. Am. Chem. Soc. 1999, 121, 10640. (j) Ni, Y.; Montgomery, J. J. Am. Chem. Soc. 2004, 43, 11162. (k) Wender, P. A.; Gamber, G. G.; Hubbard, R. D.; Zhang, L. J. Am. Chem. Soc. 2002, 124, 2876. (l) Wender, P. A.; Deschamps, N. M.; Gamber, G. G. Angew. Chem., Int. Ed. 2003, 42, 1853. (m) Wender, P. A.; Croatt, M. P.; Deschamps, N. M. J. Am. Chem. Soc. 2004, 126, 5948. (n) Wender, P. A.; Deschamps, N. M.; Williams, T. J. Angew. Chem., Int. Ed. 2004, 43, 3076.
19. For recent reviews of multicomponent reactions: (a) Dömling, A.; Ugi, I. Angew. Chem., Int. Ed. 2000, 39, 3168. (b) Tietze, L. F.; Modi, A. Med. Res. Rev. 2000, 20, 304. (c) Zhu, J. Eur. J. Org. Chem. 2003, 1133. (d) Orru, R. V. A.; de Greef, M. Synthesis 2003, 1471. (e) Bienaymé, H.; Hulme, C.; Oddon, G.; Schmitt, P. Chem. Eur. J. 2000, 6, 3321. For recent examples of multicomponent cycloadditions, see ref 8 and: f) Gilbertson, S. R.; DeBoef, B. J. Am. Chem. Soc. 2002, 124, 8784. (g) Evans, P. A.; Robinson, J. E.; Baum, E. W.; Fazal, A. N. J. Am. Chem. Soc 2002, 124, 8782. (h) Murakami, M.; Itami, K.; Ito, Y. Angew. Chem., Intl. Ed. 1998, 37, 3418. (i) Dzwiniel, T. L.; Etkin, N.; Stryker, J. M. J. Am. Chem. Soc. 1999, 121, 10640. (j) Ni, Y.; Montgomery, J. J. Am. Chem. Soc. 2004, 43, 11162. (k) Wender, P. A.; Gamber, G. G.; Hubbard, R. D.; Zhang, L. J. Am. Chem. Soc. 2002, 124, 2876. (l) Wender, P. A.; Deschamps, N. M.; Gamber, G. G. Angew. Chem., Int. Ed. 2003, 42, 1853. (m) Wender, P. A.; Croatt, M. P.; Deschamps, N. M. J. Am. Chem. Soc. 2004, 126, 5948. (n) Wender, P. A.; Deschamps, N. M.; Williams, T. J. Angew. Chem., Int. Ed. 2004, 43, 3076.
20. (a) Wender, P. A.; Ihle, N. C. J. Am. Chem. Soc. 1986, 108, 4678.
21. (b) Wender, P. A.; Nuss, J. M.; Smith, D. B.; Suárez-Sobrino, A.; Vagberg, J.; Decosta, D.; Bordner, J. J. Org. Chem. 1997, 62, 4908.
22. For the first examples, see: (a) Wender, P. A.; Jenkins, T. E. J. Am. Chem. Soc. 1989, 111, 6432. (b) Wender, P. A.; Jenkins, T. E.; Suzuki, S. J. Am. Chem. Soc. 1995, 117, 1843. For representative subsequent work, see: (c) Wender, P. A.; Smith, T. E. Tetrahedron 1998, 54, 1255. (d) Wang, B.; Cao, P.; Zhang, X. M. Tetrahedron Lett. 2000, 41, 8041. (e) Paik, S.-J.; Son, S. U.; Chung, Y. K. Org. Lett. 1999, 1, 2045. (f) Gilbertson, S. R.; Hoge, G. S.; Genov, D. G. J. Org. Chem. 1998, 63, 10077. (g) Kumar, K.; Jolly, R. S. Tetrahedron Lett. 1998, 39, 3047. (h) Murakami, M.; Ubukata, M.; Itami, K.; Ito, Y. Angew. Chem., Int. Ed. 1998, 37, 2248. (i) O'Mahoney, D. J. R.; Belanger, D. B.; Livinghouse, T. Synlett 1998, 443.
23. For the first examples, see: (a) Wender, P. A.; Jenkins, T. E. J. Am. Chem. Soc. 1989, 111, 6432. (b) Wender, P. A.; Jenkins, T. E.; Suzuki, S. J. Am. Chem. Soc. 1995, 117, 1843. For representative subsequent work, see: (c) Wender, P. A.; Smith, T. E. Tetrahedron 1998, 54, 1255. (d) Wang, B.; Cao, P.; Zhang, X. M. Tetrahedron Lett. 2000, 41, 8041. (e) Paik, S.-J.; Son, S. U.; Chung, Y. K. Org. Lett. 1999, 1, 2045. (f) Gilbertson, S. R.; Hoge, G. S.; Genov, D. G. J. Org. Chem. 1998, 63, 10077. (g) Kumar, K.; Jolly, R. S. Tetrahedron Lett. 1998, 39, 3047. (h) Murakami, M.; Ubukata, M.; Itami, K.; Ito, Y. Angew. Chem., Int. Ed. 1998, 37, 2248. (i) O'Mahoney, D. J. R.; Belanger, D. B.; Livinghouse, T. Synlett 1998, 443.
24. For the first examples, see: (a) Wender, P. A.; Jenkins, T. E. J. Am. Chem. Soc. 1989, 111, 6432. (b) Wender, P. A.; Jenkins, T. E.; Suzuki, S. J. Am. Chem. Soc. 1995, 117, 1843. For representative subsequent work, see: (c) Wender, P. A.; Smith, T. E. Tetrahedron 1998, 54, 1255. (d) Wang, B.; Cao, P.; Zhang, X. M. Tetrahedron Lett. 2000, 41, 8041. (e) Paik, S.-J.; Son, S. U.; Chung, Y. K. Org. Lett. 1999, 1, 2045. (f) Gilbertson, S. R.; Hoge, G. S.; Genov, D. G. J. Org. Chem. 1998, 63, 10077. (g) Kumar, K.; Jolly, R. S. Tetrahedron Lett. 1998, 39, 3047. (h) Murakami, M.; Ubukata, M.; Itami, K.; Ito, Y. Angew. Chem., Int. Ed. 1998, 37, 2248. (i) O'Mahoney, D. J. R.; Belanger, D. B.; Livinghouse, T. Synlett 1998, 443.
25. For the first examples, see: (a) Wender, P. A.; Jenkins, T. E. J. Am. Chem. Soc. 1989, 111, 6432. (b) Wender, P. A.; Jenkins, T. E.; Suzuki, S. J. Am. Chem. Soc. 1995, 117, 1843. For representative subsequent work, see: (c) Wender, P. A.; Smith, T. E. Tetrahedron 1998, 54, 1255. (d) Wang, B.; Cao, P.; Zhang, X. M. Tetrahedron Lett. 2000, 41, 8041. (e) Paik, S.-J.; Son, S. U.; Chung, Y. K. Org. Lett. 1999, 1, 2045. (f) Gilbertson, S. R.; Hoge, G. S.; Genov, D. G. J. Org. Chem. 1998, 63, 10077. (g) Kumar, K.; Jolly, R. S. Tetrahedron Lett. 1998, 39, 3047. (h) Murakami, M.; Ubukata, M.; Itami, K.; Ito, Y. Angew. Chem., Int. Ed. 1998, 37, 2248. (i) O'Mahoney, D. J. R.; Belanger, D. B.; Livinghouse, T. Synlett 1998, 443.
26. For the first examples, see: (a) Wender, P. A.; Jenkins, T. E. J. Am. Chem. Soc. 1989, 111, 6432. (b) Wender, P. A.; Jenkins, T. E.; Suzuki, S. J. Am. Chem. Soc. 1995, 117, 1843. For representative subsequent work, see: (c) Wender, P. A.; Smith, T. E. Tetrahedron 1998, 54, 1255. (d) Wang, B.; Cao, P.; Zhang, X. M. Tetrahedron Lett. 2000, 41, 8041. (e) Paik, S.-J.; Son, S. U.; Chung, Y. K. Org. Lett. 1999, 1, 2045. (f) Gilbertson, S. R.; Hoge, G. S.; Genov, D. G. J. Org. Chem. 1998, 63, 10077. (g) Kumar, K.; Jolly, R. S. Tetrahedron Lett. 1998, 39, 3047. (h) Murakami, M.; Ubukata, M.; Itami, K.; Ito, Y. Angew. Chem., Int. Ed. 1998, 37, 2248. (i) O'Mahoney, D. J. R.; Belanger, D. B.; Livinghouse, T. Synlett 1998, 443.
27. For the first examples, see: (a) Wender, P. A.; Jenkins, T. E. J. Am. Chem. Soc. 1989, 111, 6432. (b) Wender, P. A.; Jenkins, T. E.; Suzuki, S. J. Am. Chem. Soc. 1995, 117, 1843. For representative subsequent work, see: (c) Wender, P. A.; Smith, T. E. Tetrahedron 1998, 54, 1255. (d) Wang, B.; Cao, P.; Zhang, X. M. Tetrahedron Lett. 2000, 41, 8041. (e) Paik, S.-J.; Son, S. U.; Chung, Y. K. Org. Lett. 1999, 1, 2045. (f) Gilbertson, S. R.; Hoge, G. S.; Genov, D. G. J. Org. Chem. 1998, 63, 10077. (g) Kumar, K.; Jolly, R. S. Tetrahedron Lett. 1998, 39, 3047. (h) Murakami, M.; Ubukata, M.; Itami, K.; Ito, Y. Angew. Chem., Int. Ed. 1998, 37, 2248. (i) O'Mahoney, D. J. R.; Belanger, D. B.; Livinghouse, T. Synlett 1998, 443.
28. For the first examples, see: (a) Wender, P. A.; Jenkins, T. E. J. Am. Chem. Soc. 1989, 111, 6432. (b) Wender, P. A.; Jenkins, T. E.; Suzuki, S. J. Am. Chem. Soc. 1995, 117, 1843. For representative subsequent work, see: (c) Wender, P. A.; Smith, T. E. Tetrahedron 1998, 54, 1255. (d) Wang, B.; Cao, P.; Zhang, X. M. Tetrahedron Lett. 2000, 41, 8041. (e) Paik, S.-J.; Son, S. U.; Chung, Y. K. Org. Lett. 1999, 1, 2045. (f) Gilbertson, S. R.; Hoge, G. S.; Genov, D. G. J. Org. Chem. 1998, 63, 10077. (g) Kumar, K.; Jolly, R. S. Tetrahedron Lett. 1998, 39, 3047. (h) Murakami, M.; Ubukata, M.; Itami, K.; Ito, Y. Angew. Chem., Int. Ed. 1998, 37, 2248. (i) O'Mahoney, D. J. R.; Belanger, D. B.; Livinghouse, T. Synlett 1998, 443.
29. For the first examples, see: (a) Wender, P. A.; Jenkins, T. E. J. Am. Chem. Soc. 1989, 111, 6432. (b) Wender, P. A.; Jenkins, T. E.; Suzuki, S. J. Am. Chem. Soc. 1995, 117, 1843. For representative subsequent work, see: (c) Wender, P. A.; Smith, T. E. Tetrahedron 1998, 54, 1255. (d) Wang, B.; Cao, P.; Zhang, X. M. Tetrahedron Lett. 2000, 41, 8041. (e) Paik, S.-J.; Son, S. U.; Chung, Y. K. Org. Lett. 1999, 1, 2045. (f) Gilbertson, S. R.; Hoge, G. S.; Genov, D. G. J. Org. Chem. 1998, 63, 10077. (g) Kumar, K.; Jolly, R. S. Tetrahedron Lett. 1998, 39, 3047. (h) Murakami, M.; Ubukata, M.; Itami, K.; Ito, Y. Angew. Chem., Int. Ed. 1998, 37, 2248. (i) O'Mahoney, D. J. R.; Belanger, D. B.; Livinghouse, T. Synlett 1998, 443.
30. For the first examples, see: (a) Wender, P. A.; Jenkins, T. E. J. Am. Chem. Soc. 1989, 111, 6432. (b) Wender, P. A.; Jenkins, T. E.; Suzuki, S. J. Am. Chem. Soc. 1995, 117, 1843. For representative subsequent work, see: (c) Wender, P. A.; Smith, T. E. Tetrahedron 1998, 54, 1255. (d) Wang, B.; Cao, P.; Zhang, X. M. Tetrahedron Lett. 2000, 41, 8041. (e) Paik, S.-J.; Son, S. U.; Chung, Y. K. Org. Lett. 1999, 1, 2045. (f) Gilbertson, S. R.; Hoge, G. S.; Genov, D. G. J. Org. Chem. 1998, 63, 10077. (g) Kumar, K.; Jolly, R. S. Tetrahedron Lett. 1998, 39, 3047. (h) Murakami, M.; Ubukata, M.; Itami, K.; Ito, Y. Angew. Chem., Int. Ed. 1998, 37, 2248. (i) O'Mahoney, D. J. R.; Belanger, D. B.; Livinghouse, T. Synlett 1998, 443.
31. For the first examples, see: (a) Wender, P. A.; Takahashi, H.; Witulski, B. J. Am. Chem. Soc. 1995, 117, 4720. (b) Wender, P. A.; Rieck, H.; Fuji, M. J. Am. Chem. Soc. 1998, 120, 10976. For representative recent work, see: (c) Wender, P. A.; Love, J. A.; Williams, T. J. Synlett 2003, 1295. (d) Wender, P. A.; Williams, T. J. Angew. Chem., Int. Ed. 2002, 41, 4550. (e) Wender, P. A.; Pedersen, T. M.; Scanio, M. J. C. J. Am. Chem. Soc. 2002, 124, 15154. (f) Wender, P. A.; Gamber, G. G.; Scanio, M. J. C. Angew. Chem., Int. Ed. 2001, 40, 3895. (g) Wender, P. A.; Barzilay, C. M.; Dyckman, A. J. J. Am. Chem. Soc. 2001, 123, 179. (h) Wender, P. A.; Dyckman, A. J.; Husfeld, C. O.; Scanio, M. J. C. Org. Lett. 2000, 2, 1609. (i) Trost, B. M.; Shen, H. C.; Schultz, T.; Koradin, C.; Shirock, H. Org. Lett. 2003, 5, 4149.
32. For the first examples, see: (a) Wender, P. A.; Takahashi, H.; Witulski, B. J. Am. Chem. Soc. 1995, 117, 4720. (b) Wender, P. A.; Rieck, H.; Fuji, M. J. Am. Chem. Soc. 1998, 120, 10976. For representative recent work, see: (c) Wender, P. A.; Love, J. A.; Williams, T. J. Synlett 2003, 1295. (d) Wender, P. A.; Williams, T. J. Angew. Chem., Int. Ed. 2002, 41, 4550. (e) Wender, P. A.; Pedersen, T. M.; Scanio, M. J. C. J. Am. Chem. Soc. 2002, 124, 15154. (f) Wender, P. A.; Gamber, G. G.; Scanio, M. J. C. Angew. Chem., Int. Ed. 2001, 40, 3895. (g) Wender, P. A.; Barzilay, C. M.; Dyckman, A. J. J. Am. Chem. Soc. 2001, 123, 179. (h) Wender, P. A.; Dyckman, A. J.; Husfeld, C. O.; Scanio, M. J. C. Org. Lett. 2000, 2, 1609. (i) Trost, B. M.; Shen, H. C.; Schultz, T.; Koradin, C.; Shirock, H. Org. Lett. 2003, 5, 4149.
33. For the first examples, see: (a) Wender, P. A.; Takahashi, H.; Witulski, B. J. Am. Chem. Soc. 1995, 117, 4720. (b) Wender, P. A.; Rieck, H.; Fuji, M. J. Am. Chem. Soc. 1998, 120, 10976. For representative recent work, see: (c) Wender, P. A.; Love, J. A.; Williams, T. J. Synlett 2003, 1295. (d) Wender, P. A.; Williams, T. J. Angew. Chem., Int. Ed. 2002, 41, 4550. (e) Wender, P. A.; Pedersen, T. M.; Scanio, M. J. C. J. Am. Chem. Soc. 2002, 124, 15154. (f) Wender, P. A.; Gamber, G. G.; Scanio, M. J. C. Angew. Chem., Int. Ed. 2001, 40, 3895. (g) Wender, P. A.; Barzilay, C. M.; Dyckman, A. J. J. Am. Chem. Soc. 2001, 123, 179. (h) Wender, P. A.; Dyckman, A. J.; Husfeld, C. O.; Scanio, M. J. C. Org. Lett. 2000, 2, 1609. (i) Trost, B. M.; Shen, H. C.; Schultz, T.; Koradin, C.; Shirock, H. Org. Lett. 2003, 5, 4149.
34. For the first examples, see: (a) Wender, P. A.; Takahashi, H.; Witulski, B. J. Am. Chem. Soc. 1995, 117, 4720. (b) Wender, P. A.; Rieck, H.; Fuji, M. J. Am. Chem. Soc. 1998, 120, 10976. For representative recent work, see: (c) Wender, P. A.; Love, J. A.; Williams, T. J. Synlett 2003, 1295. (d) Wender, P. A.; Williams, T. J. Angew. Chem., Int. Ed. 2002, 41, 4550. (e) Wender, P. A.; Pedersen, T. M.; Scanio, M. J. C. J. Am. Chem. Soc. 2002, 124, 15154. (f) Wender, P. A.; Gamber, G. G.; Scanio, M. J. C. Angew. Chem., Int. Ed. 2001, 40, 3895. (g) Wender, P. A.; Barzilay, C. M.; Dyckman, A. J. J. Am. Chem. Soc. 2001, 123, 179. (h) Wender, P. A.; Dyckman, A. J.; Husfeld, C. O.; Scanio, M. J. C. Org. Lett. 2000, 2, 1609. (i) Trost, B. M.; Shen, H. C.; Schultz, T.; Koradin, C.; Shirock, H. Org. Lett. 2003, 5, 4149.
35. For the first examples, see: (a) Wender, P. A.; Takahashi, H.; Witulski, B. J. Am. Chem. Soc. 1995, 117, 4720. (b) Wender, P. A.; Rieck, H.; Fuji, M. J. Am. Chem. Soc. 1998, 120, 10976. For representative recent work, see: (c) Wender, P. A.; Love, J. A.; Williams, T. J. Synlett 2003, 1295. (d) Wender, P. A.; Williams, T. J. Angew. Chem., Int. Ed. 2002, 41, 4550. (e) Wender, P. A.; Pedersen, T. M.; Scanio, M. J. C. J. Am. Chem. Soc. 2002, 124, 15154. (f) Wender, P. A.; Gamber, G. G.; Scanio, M. J. C. Angew. Chem., Int. Ed. 2001, 40, 3895. (g) Wender, P. A.; Barzilay, C. M.; Dyckman, A. J. J. Am. Chem. Soc. 2001, 123, 179. (h) Wender, P. A.; Dyckman, A. J.; Husfeld, C. O.; Scanio, M. J. C. Org. Lett. 2000, 2, 1609. (i) Trost, B. M.; Shen, H. C.; Schultz, T.; Koradin, C.; Shirock, H. Org. Lett. 2003, 5, 4149.
36. For the first examples, see: (a) Wender, P. A.; Takahashi, H.; Witulski, B. J. Am. Chem. Soc. 1995, 117, 4720. (b) Wender, P. A.; Rieck, H.; Fuji, M. J. Am. Chem. Soc. 1998, 120, 10976. For representative recent work, see: (c) Wender, P. A.; Love, J. A.; Williams, T. J. Synlett 2003, 1295. (d) Wender, P. A.; Williams, T. J. Angew. Chem., Int. Ed. 2002, 41, 4550. (e) Wender, P. A.; Pedersen, T. M.; Scanio, M. J. C. J. Am. Chem. Soc. 2002, 124, 15154. (f) Wender, P. A.; Gamber, G. G.; Scanio, M. J. C. Angew. Chem., Int. Ed. 2001, 40, 3895. (g) Wender, P. A.; Barzilay, C. M.; Dyckman, A. J. J. Am. Chem. Soc. 2001, 123, 179. (h) Wender, P. A.; Dyckman, A. J.; Husfeld, C. O.; Scanio, M. J. C. Org. Lett. 2000, 2, 1609. (i) Trost, B. M.; Shen, H. C.; Schultz, T.; Koradin, C.; Shirock, H. Org. Lett. 2003, 5, 4149.
37. For the first examples, see: (a) Wender, P. A.; Takahashi, H.; Witulski, B. J. Am. Chem. Soc. 1995, 117, 4720. (b) Wender, P. A.; Rieck, H.; Fuji, M. J. Am. Chem. Soc. 1998, 120, 10976. For representative recent work, see: (c) Wender, P. A.; Love, J. A.; Williams, T. J. Synlett 2003, 1295. (d) Wender, P. A.; Williams, T. J. Angew. Chem., Int. Ed. 2002, 41, 4550. (e) Wender, P. A.; Pedersen, T. M.; Scanio, M. J. C. J. Am. Chem. Soc. 2002, 124, 15154. (f) Wender, P. A.; Gamber, G. G.; Scanio, M. J. C. Angew. Chem., Int. Ed. 2001, 40, 3895. (g) Wender, P. A.; Barzilay, C. M.; Dyckman, A. J. J. Am. Chem. Soc. 2001, 123, 179. (h) Wender, P. A.; Dyckman, A. J.; Husfeld, C. O.; Scanio, M. J. C. Org. Lett. 2000, 2, 1609. (i) Trost, B. M.; Shen, H. C.; Schultz, T.; Koradin, C.; Shirock, H. Org. Lett. 2003, 5, 4149.
38. For the first examples, see: (a) Wender, P. A.; Takahashi, H.; Witulski, B. J. Am. Chem. Soc. 1995, 117, 4720. (b) Wender, P. A.; Rieck, H.; Fuji, M. J. Am. Chem. Soc. 1998, 120, 10976. For representative recent work, see: (c) Wender, P. A.; Love, J. A.; Williams, T. J. Synlett 2003, 1295. (d) Wender, P. A.; Williams, T. J. Angew. Chem., Int. Ed. 2002, 41, 4550. (e) Wender, P. A.; Pedersen, T. M.; Scanio, M. J. C. J. Am. Chem. Soc. 2002, 124, 15154. (f) Wender, P. A.; Gamber, G. G.; Scanio, M. J. C. Angew. Chem., Int. Ed. 2001, 40, 3895. (g) Wender, P. A.; Barzilay, C. M.; Dyckman, A. J. J. Am. Chem. Soc. 2001, 123, 179. (h) Wender, P. A.; Dyckman, A. J.; Husfeld, C. O.; Scanio, M. J. C. Org. Lett. 2000, 2, 1609. (i) Trost, B. M.; Shen, H. C.; Schultz, T.; Koradin, C.; Shirock, H. Org. Lett. 2003, 5, 4149.
39. For the first examples, see: (a) Wender, P. A.; Takahashi, H.; Witulski, B. J. Am. Chem. Soc. 1995, 117, 4720. (b) Wender, P. A.; Rieck, H.; Fuji, M. J. Am. Chem. Soc. 1998, 120, 10976. For representative recent work, see: (c) Wender, P. A.; Love, J. A.; Williams, T. J. Synlett 2003, 1295. (d) Wender, P. A.; Williams, T. J. Angew. Chem., Int. Ed. 2002, 41, 4550. (e) Wender, P. A.; Pedersen, T. M.; Scanio, M. J. C. J. Am. Chem. Soc. 2002, 124, 15154. (f) Wender, P. A.; Gamber, G. G.; Scanio, M. J. C. Angew. Chem., Int. Ed. 2001, 40, 3895. (g) Wender, P. A.; Barzilay, C. M.; Dyckman, A. J. J. Am. Chem. Soc. 2001, 123, 179. (h) Wender, P. A.; Dyckman, A. J.; Husfeld, C. O.; Scanio, M. J. C. Org. Lett. 2000, 2, 1609. (i) Trost, B. M.; Shen, H. C.; Schultz, T.; Koradin, C.; Shirock, H. Org. Lett. 2003, 5, 4149.
40. Wender, P. A.; Correa, A. G.; Sato, Y.; Sun, R. J. Am. Chem. Soc. 2000, 122, 7815.
41. For reviews of metal-catalyzed cycloadditions, see: (a) Aubert, C.; Buisine, O.; Malacria, M. Chem. Rev. 2002, 102, 813. (b) Yet, L. Chem Rev. 2000, 100, 2963. (c) Lautens, M.; Klute, W.; Tam, W. Chem. Rev. 1996, 96, 49. (d) Ojima, I.; Tzamarioudaki, M.; Li, Z.; Donovan, R. J. Chem. Rev. 1996, 96, 635.
42. For reviews of metal-catalyzed cycloadditions, see: (a) Aubert, C.; Buisine, O.; Malacria, M. Chem. Rev. 2002, 102, 813. (b) Yet, L. Chem Rev. 2000, 100, 2963. (c) Lautens, M.; Klute, W.; Tam, W. Chem. Rev. 1996, 96, 49. (d) Ojima, I.; Tzamarioudaki, M.; Li, Z.; Donovan, R. J. Chem. Rev. 1996, 96, 635.
43. For reviews of metal-catalyzed cycloadditions, see: (a) Aubert, C.; Buisine, O.; Malacria, M. Chem. Rev. 2002, 102, 813. (b) Yet, L. Chem Rev. 2000, 100, 2963. (c) Lautens, M.; Klute, W.; Tam, W. Chem. Rev. 1996, 96, 49. (d) Ojima, I.; Tzamarioudaki, M.; Li, Z.; Donovan, R. J. Chem. Rev. 1996, 96, 635.
44. For reviews of metal-catalyzed cycloadditions, see: (a) Aubert, C.; Buisine, O.; Malacria, M. Chem. Rev. 2002, 102, 813. (b) Yet, L. Chem Rev. 2000, 100, 2963. (c) Lautens, M.; Klute, W.; Tam, W. Chem. Rev. 1996, 96, 49. (d) Ojima, I.; Tzamarioudaki, M.; Li, Z.; Donovan, R. J. Chem. Rev. 1996, 96, 635.
45. Biaryl ligands: (a) Kocovsky, P.; Vyskocil, S.; Smrcina, M. Chem. Rev. 2003, 103, 3213. (b) Chen, Y.; Yekta, S.; Yudin, A. K. Chem. Rev. 2003, 103, 3155. (c) Walsh, P. J.; Lurain, A. E.; Balsells, J. Chem. Rev. 2003, 103, 3297. Indenyl ligands: (d) Stradiotto, M.; McGlinchy, M. J. Coord. Chem. Rev. 2001, 219, 311. (e) Zargarian, D. Coord. Chem. Rev. 2002, 233-234, 157. (f) Cadierno, V.; Diez, J.; Gamasa, M. P.; Gimeno, J.; Lastra, E. Coord. Chem. Rev. 1999, 195, 147.
46. Biaryl ligands: (a) Kocovsky, P.; Vyskocil, S.; Smrcina, M. Chem. Rev. 2003, 103, 3213. (b) Chen, Y.; Yekta, S.; Yudin, A. K. Chem. Rev. 2003, 103, 3155. (c) Walsh, P. J.; Lurain, A. E.; Balsells, J. Chem. Rev. 2003, 103, 3297. Indenyl ligands: (d) Stradiotto, M.; McGlinchy, M. J. Coord. Chem. Rev. 2001, 219, 311. (e) Zargarian, D. Coord. Chem. Rev. 2002, 233-234, 157. (f) Cadierno, V.; Diez, J.; Gamasa, M. P.; Gimeno, J.; Lastra, E. Coord. Chem. Rev. 1999, 195, 147.
47. Biaryl ligands: (a) Kocovsky, P.; Vyskocil, S.; Smrcina, M. Chem. Rev. 2003, 103, 3213. (b) Chen, Y.; Yekta, S.; Yudin, A. K. Chem. Rev. 2003, 103, 3155. (c) Walsh, P. J.; Lurain, A. E.; Balsells, J. Chem. Rev. 2003, 103, 3297. Indenyl ligands: (d) Stradiotto, M.; McGlinchy, M. J. Coord. Chem. Rev. 2001, 219, 311. (e) Zargarian, D. Coord. Chem. Rev. 2002, 233-234, 157. (f) Cadierno, V.; Diez, J.; Gamasa, M. P.; Gimeno, J.; Lastra, E. Coord. Chem. Rev. 1999, 195, 147.
48. Biaryl ligands: (a) Kocovsky, P.; Vyskocil, S.; Smrcina, M. Chem. Rev. 2003, 103, 3213. (b) Chen, Y.; Yekta, S.; Yudin, A. K. Chem. Rev. 2003, 103, 3155. (c) Walsh, P. J.; Lurain, A. E.; Balsells, J. Chem. Rev. 2003, 103, 3297. Indenyl ligands: (d) Stradiotto, M.; McGlinchy, M. J. Coord. Chem. Rev. 2001, 219, 311. (e) Zargarian, D. Coord. Chem. Rev. 2002, 233-234, 157. (f) Cadierno, V.; Diez, J.; Gamasa, M. P.; Gimeno, J.; Lastra, E. Coord. Chem. Rev. 1999, 195, 147.
49. Biaryl ligands: (a) Kocovsky, P.; Vyskocil, S.; Smrcina, M. Chem. Rev. 2003, 103, 3213. (b) Chen, Y.; Yekta, S.; Yudin, A. K. Chem. Rev. 2003, 103, 3155. (c) Walsh, P. J.; Lurain, A. E.; Balsells, J. Chem. Rev. 2003, 103, 3297. Indenyl ligands: (d) Stradiotto, M.; McGlinchy, M. J. Coord. Chem. Rev. 2001, 219, 311. (e) Zargarian, D. Coord. Chem. Rev. 2002, 233-234, 157. (f) Cadierno, V.; Diez, J.; Gamasa, M. P.; Gimeno, J.; Lastra, E. Coord. Chem. Rev. 1999, 195, 147.
50. Biaryl ligands: (a) Kocovsky, P.; Vyskocil, S.; Smrcina, M. Chem. Rev. 2003, 103, 3213. (b) Chen, Y.; Yekta, S.; Yudin, A. K. Chem. Rev. 2003, 103, 3155. (c) Walsh, P. J.; Lurain, A. E.; Balsells, J. Chem. Rev. 2003, 103, 3297. Indenyl ligands: (d) Stradiotto, M.; McGlinchy, M. J. Coord. Chem. Rev. 2001, 219, 311. (e) Zargarian, D. Coord. Chem. Rev. 2002, 233-234, 157. (f) Cadierno, V.; Diez, J.; Gamasa, M. P.; Gimeno, J.; Lastra, E. Coord. Chem. Rev. 1999, 195, 147.
51. For recent examples of a biaryl sensor and materials: (a) Jiao, G.-S.; Thorensen, L. H.; Burgess, K. J. Am. Chem. Soc. 2003, 125, 14668. (b) Kozaki, M.; Okada, K. Org. Lett. 2004, 5, 485. For indanone derived chromaphors: (c) Janowska, I.; Zakrzewski, J.; Nakatani, K.; Delaire, J. A.; Palusaik, M.; Walak, M.; Scholl, H. J. Organomet. Chem. 2003, 675, 35.
52. For recent examples of a biaryl sensor and materials: (a) Jiao, G.-S.; Thorensen, L. H.; Burgess, K. J. Am. Chem. Soc. 2003, 125, 14668. (b) Kozaki, M.; Okada, K. Org. Lett. 2004, 5, 485. For indanone derived chromaphors: (c) Janowska, I.; Zakrzewski, J.; Nakatani, K.; Delaire, J. A.; Palusaik, M.; Walak, M.; Scholl, H. J. Organomet. Chem. 2003, 675, 35.
53. For recent examples of a biaryl sensor and materials: (a) Jiao, G.-S.; Thorensen, L. H.; Burgess, K. J. Am. Chem. Soc. 2003, 125, 14668. (b) Kozaki, M.; Okada, K. Org. Lett. 2004, 5, 485. For indanone derived chromaphors: (c) Janowska, I.; Zakrzewski, J.; Nakatani, K.; Delaire, J. A.; Palusaik, M.; Walak, M.; Scholl, H. J. Organomet. Chem. 2003, 675, 35.
54. For a recent example of a terphenyl α-helix mimic: (a) Kutzi, O.; Park, H. S.; Ernst, J. T.; Orner, B. P.; Yin, H.; Hamilton, A. D. J. Am. Chem. Soc. 2002, 124, 11838. For recent examples of indanone derivatives: (b) Leoni, L. M.; Hamel, E.; Genini, D.; Shih, H.; Carrera, C. J.; Cottam, H. B.; Carson, D. A. J. Natl. Cancer Inst. 2000, 92, 217. (c) Klein, T.; Nüsing, R. M.; Wiesenberg-Boettcher, I.; Ullrich, V. Biochem. Pharmacol. 1996, 51, 285. (d) Saxena, A.; Fedorko, J. M.; Vinayaka, C. R.; Medhekar, R.; Radic, Z.; Taylor, P.; Lockridge, O.; Doctor, B. P. Eur. J. Biochem. 2003, 270, 4447.
55. For a recent example of a terphenyl α-helix mimic: (a) Kutzi, O.; Park, H. S.; Ernst, J. T.; Orner, B. P.; Yin, H.; Hamilton, A. D. J. Am. Chem. Soc. 2002, 124, 11838. For recent examples of indanone derivatives: (b) Leoni, L. M.; Hamel, E.; Genini, D.; Shih, H.; Carrera, C. J.; Cottam, H. B.; Carson, D. A. J. Natl. Cancer Inst. 2000, 92, 217. (c) Klein, T.; Nüsing, R. M.; Wiesenberg-Boettcher, I.; Ullrich, V. Biochem. Pharmacol. 1996, 51, 285. (d) Saxena, A.; Fedorko, J. M.; Vinayaka, C. R.; Medhekar, R.; Radic, Z.; Taylor, P.; Lockridge, O.; Doctor, B. P. Eur. J. Biochem. 2003, 270, 4447.
56. For a recent example of a terphenyl α-helix mimic: (a) Kutzi, O.; Park, H. S.; Ernst, J. T.; Orner, B. P.; Yin, H.; Hamilton, A. D. J. Am. Chem. Soc. 2002, 124, 11838. For recent examples of indanone derivatives: (b) Leoni, L. M.; Hamel, E.; Genini, D.; Shih, H.; Carrera, C. J.; Cottam, H. B.; Carson, D. A. J. Natl. Cancer Inst. 2000, 92, 217. (c) Klein, T.; Nüsing, R. M.; Wiesenberg-Boettcher, I.; Ullrich, V. Biochem. Pharmacol. 1996, 51, 285. (d) Saxena, A.; Fedorko, J. M.; Vinayaka, C. R.; Medhekar, R.; Radic, Z.; Taylor, P.; Lockridge, O.; Doctor, B. P. Eur. J. Biochem. 2003, 270, 4447.
57. For a recent example of a terphenyl α-helix mimic: (a) Kutzi, O.; Park, H. S.; Ernst, J. T.; Orner, B. P.; Yin, H.; Hamilton, A. D. J. Am. Chem. Soc. 2002, 124, 11838. For recent examples of indanone derivatives: (b) Leoni, L. M.; Hamel, E.; Genini, D.; Shih, H.; Carrera, C. J.; Cottam, H. B.; Carson, D. A. J. Natl. Cancer Inst. 2000, 92, 217. (c) Klein, T.; Nüsing, R. M.; Wiesenberg-Boettcher, I.; Ullrich, V. Biochem. Pharmacol. 1996, 51, 285. (d) Saxena, A.; Fedorko, J. M.; Vinayaka, C. R.; Medhekar, R.; Radic, Z.; Taylor, P.; Lockridge, O.; Doctor, B. P. Eur. J. Biochem. 2003, 270, 4447.
58. For recent examples of biaryl derivatives: (a) Lloyd-Williams, P.; Giralt, E. Chem. Soc. Rev. 2001, 30, 145. For recent examples of indanone derivatives: (b) Cossy, J.; Belotti, D.; Maguer, A. Synlett 2003, 1515. (c) Tietze, L. F.; Ramachandar, T.; Vock, C. Synlett 2003, 118.
59. For recent examples of biaryl derivatives: (a) Lloyd-Williams, P.; Giralt, E. Chem. Soc. Rev. 2001, 30, 145. For recent examples of indanone derivatives: (b) Cossy, J.; Belotti, D.; Maguer, A. Synlett 2003, 1515. (c) Tietze, L. F.; Ramachandar, T.; Vock, C. Synlett 2003, 118.
60. For recent examples of biaryl derivatives: (a) Lloyd-Williams, P.; Giralt, E. Chem. Soc. Rev. 2001, 30, 145. For recent examples of indanone derivatives: (b) Cossy, J.; Belotti, D.; Maguer, A. Synlett 2003, 1515. (c) Tietze, L. F.; Ramachandar, T.; Vock, C. Synlett 2003, 118.
61. (a) Wender, P. A.; Dyckman, A. J.; Husfeld, C. O.; Kadereit, D.; Love, J. A.; Reick, H. J. Am. Chem. Soc. 1999, 121, 10442.
62. (b) Wender, P. A.; Dyckman, A. J. Org. Lett. 1999, 1, 2089.