Highly regioselective radical cyclizations of allenamides

Organic Letters

Volumn 7, Issue 5, 2005, Pages 775-778

  Shen, Lichun ^a   Hsung, Richard P ^a  

^a University of Minnesota   (United States)

Author keywords

[No Author keywords available]

Indexed keywords

ALLENE DERIVATIVE; AMIDE; CARBON; INDAN DERIVATIVE; ISOINDOLE DERIVATIVE; ISOQUINOLINE DERIVATIVE; NAPHTHALENE DERIVATIVE; NITROGEN;

ARTICLE; CHEMICAL PROCEDURES; CHEMICAL REACTION; CYCLIZATION; FEASIBILITY STUDY; REACTION ANALYSIS;

EID: 15044348918     PISSN: 15237060     EISSN: None     Source Type: Journal    
DOI: 10.1021/ol047572z     Document Type: Article

References (55)

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16. For recent allenamide chemistry, see: (a) Añorbe, L.; Poblador, A.; Domínguez, G.; Pérez-Castells, J. Tetrahedron Lett. 2004, 45, 4441. (b) Achmatowicz, M.; Hegedus, L. S. J. Org. Chem. 2004, 69, 2229. (c) Ranslow, P. D. B.; Hegedus, L. S.; de los Rios, C. J. Org. Chem. 2004, 69, 105. (d) Bacci, J. P.; Greenman, K. L.; Van Vranken, D. L. J. Org. Chem. 2003, 68, 4955. (e) Armstrong, A.; Cooke, R. S.; Shanahan, S. E. Org. Biomol. Chem. 2003, 1, 3142. (f) Gaul C.; Seebach, D. Helv. Chim. Acta 2002, 85, 963. (g) Kozawa, Y.; Mori, M. Tetrahedron Lett. 2002, 43, 1499. (h) Nair, V.; Sethumadhavan, D.; Nair, S. M.; Shanmugam, P.; Treesa, P. M.; Eigendorf, G. K. Synthesis 2002, 1655. (i) Kozawa, Y.; Mori, M. Tetrahedron Lett. 2001, 42, 4869. (j) Kinderman, S. S.; van Maarseveen, J. H.; Schoemaker, H. E.; Hiemstra, H.; Rutjes, F. P. T., Org. Lett. 2001, 3, 2045. (k) van Boxtel, L. J.; Korbe, S.; Noltemeyer, M.; de Meijere, A. Eur. J. Org. Chem. 2001, 2283. (l) Grigg, R.; Köppen, I.; Rasparini, M.; Sridharan, V. Chem. Commun. 2001, 964. (m) For papers before 2001, see ref 5.
17. For recent allenamide chemistry, see: (a) Añorbe, L.; Poblador, A.; Domínguez, G.; Pérez-Castells, J. Tetrahedron Lett. 2004, 45, 4441. (b) Achmatowicz, M.; Hegedus, L. S. J. Org. Chem. 2004, 69, 2229. (c) Ranslow, P. D. B.; Hegedus, L. S.; de los Rios, C. J. Org. Chem. 2004, 69, 105. (d) Bacci, J. P.; Greenman, K. L.; Van Vranken, D. L. J. Org. Chem. 2003, 68, 4955. (e) Armstrong, A.; Cooke, R. S.; Shanahan, S. E. Org. Biomol. Chem. 2003, 1, 3142. (f) Gaul C.; Seebach, D. Helv. Chim. Acta 2002, 85, 963. (g) Kozawa, Y.; Mori, M. Tetrahedron Lett. 2002, 43, 1499. (h) Nair, V.; Sethumadhavan, D.; Nair, S. M.; Shanmugam, P.; Treesa, P. M.; Eigendorf, G. K. Synthesis 2002, 1655. (i) Kozawa, Y.; Mori, M. Tetrahedron Lett. 2001, 42, 4869. (j) Kinderman, S. S.; van Maarseveen, J. H.; Schoemaker, H. E.; Hiemstra, H.; Rutjes, F. P. T., Org. Lett. 2001, 3, 2045. (k) van Boxtel, L. J.; Korbe, S.; Noltemeyer, M.; de Meijere, A. Eur. J. Org. Chem. 2001, 2283. (l) Grigg, R.; Köppen, I.; Rasparini, M.; Sridharan, V. Chem. Commun. 2001, 964. (m) For papers before 2001, see ref 5.
18. For recent allenamide chemistry, see: (a) Añorbe, L.; Poblador, A.; Domínguez, G.; Pérez-Castells, J. Tetrahedron Lett. 2004, 45, 4441. (b) Achmatowicz, M.; Hegedus, L. S. J. Org. Chem. 2004, 69, 2229. (c) Ranslow, P. D. B.; Hegedus, L. S.; de los Rios, C. J. Org. Chem. 2004, 69, 105. (d) Bacci, J. P.; Greenman, K. L.; Van Vranken, D. L. J. Org. Chem. 2003, 68, 4955. (e) Armstrong, A.; Cooke, R. S.; Shanahan, S. E. Org. Biomol. Chem. 2003, 1, 3142. (f) Gaul C.; Seebach, D. Helv. Chim. Acta 2002, 85, 963. (g) Kozawa, Y.; Mori, M. Tetrahedron Lett. 2002, 43, 1499. (h) Nair, V.; Sethumadhavan, D.; Nair, S. M.; Shanmugam, P.; Treesa, P. M.; Eigendorf, G. K. Synthesis 2002, 1655. (i) Kozawa, Y.; Mori, M. Tetrahedron Lett. 2001, 42, 4869. (j) Kinderman, S. S.; van Maarseveen, J. H.; Schoemaker, H. E.; Hiemstra, H.; Rutjes, F. P. T., Org. Lett. 2001, 3, 2045. (k) van Boxtel, L. J.; Korbe, S.; Noltemeyer, M.; de Meijere, A. Eur. J. Org. Chem. 2001, 2283. (l) Grigg, R.; Köppen, I.; Rasparini, M.; Sridharan, V. Chem. Commun. 2001, 964. (m) For papers before 2001, see ref 5.
19. For recent allenamide chemistry, see: (a) Añorbe, L.; Poblador, A.; Domínguez, G.; Pérez-Castells, J. Tetrahedron Lett. 2004, 45, 4441. (b) Achmatowicz, M.; Hegedus, L. S. J. Org. Chem. 2004, 69, 2229. (c) Ranslow, P. D. B.; Hegedus, L. S.; de los Rios, C. J. Org. Chem. 2004, 69, 105. (d) Bacci, J. P.; Greenman, K. L.; Van Vranken, D. L. J. Org. Chem. 2003, 68, 4955. (e) Armstrong, A.; Cooke, R. S.; Shanahan, S. E. Org. Biomol. Chem. 2003, 1, 3142. (f) Gaul C.; Seebach, D. Helv. Chim. Acta 2002, 85, 963. (g) Kozawa, Y.; Mori, M. Tetrahedron Lett. 2002, 43, 1499. (h) Nair, V.; Sethumadhavan, D.; Nair, S. M.; Shanmugam, P.; Treesa, P. M.; Eigendorf, G. K. Synthesis 2002, 1655. (i) Kozawa, Y.; Mori, M. Tetrahedron Lett. 2001, 42, 4869. (j) Kinderman, S. S.; van Maarseveen, J. H.; Schoemaker, H. E.; Hiemstra, H.; Rutjes, F. P. T., Org. Lett. 2001, 3, 2045. (k) van Boxtel, L. J.; Korbe, S.; Noltemeyer, M.; de Meijere, A. Eur. J. Org. Chem. 2001, 2283. (l) Grigg, R.; Köppen, I.; Rasparini, M.; Sridharan, V. Chem. Commun. 2001, 964. (m) For papers before 2001, see ref 5.
20. For recent allenamide chemistry, see: (a) Añorbe, L.; Poblador, A.; Domínguez, G.; Pérez-Castells, J. Tetrahedron Lett. 2004, 45, 4441. (b) Achmatowicz, M.; Hegedus, L. S. J. Org. Chem. 2004, 69, 2229. (c) Ranslow, P. D. B.; Hegedus, L. S.; de los Rios, C. J. Org. Chem. 2004, 69, 105. (d) Bacci, J. P.; Greenman, K. L.; Van Vranken, D. L. J. Org. Chem. 2003, 68, 4955. (e) Armstrong, A.; Cooke, R. S.; Shanahan, S. E. Org. Biomol. Chem. 2003, 1, 3142. (f) Gaul C.; Seebach, D. Helv. Chim. Acta 2002, 85, 963. (g) Kozawa, Y.; Mori, M. Tetrahedron Lett. 2002, 43, 1499. (h) Nair, V.; Sethumadhavan, D.; Nair, S. M.; Shanmugam, P.; Treesa, P. M.; Eigendorf, G. K. Synthesis 2002, 1655. (i) Kozawa, Y.; Mori, M. Tetrahedron Lett. 2001, 42, 4869. (j) Kinderman, S. S.; van Maarseveen, J. H.; Schoemaker, H. E.; Hiemstra, H.; Rutjes, F. P. T., Org. Lett. 2001, 3, 2045. (k) van Boxtel, L. J.; Korbe, S.; Noltemeyer, M.; de Meijere, A. Eur. J. Org. Chem. 2001, 2283. (l) Grigg, R.; Köppen, I.; Rasparini, M.; Sridharan, V. Chem. Commun. 2001, 964. (m) For papers before 2001, see ref 5.
21. For recent allenamide chemistry, see: (a) Añorbe, L.; Poblador, A.; Domínguez, G.; Pérez-Castells, J. Tetrahedron Lett. 2004, 45, 4441. (b) Achmatowicz, M.; Hegedus, L. S. J. Org. Chem. 2004, 69, 2229. (c) Ranslow, P. D. B.; Hegedus, L. S.; de los Rios, C. J. Org. Chem. 2004, 69, 105. (d) Bacci, J. P.; Greenman, K. L.; Van Vranken, D. L. J. Org. Chem. 2003, 68, 4955. (e) Armstrong, A.; Cooke, R. S.; Shanahan, S. E. Org. Biomol. Chem. 2003, 1, 3142. (f) Gaul C.; Seebach, D. Helv. Chim. Acta 2002, 85, 963. (g) Kozawa, Y.; Mori, M. Tetrahedron Lett. 2002, 43, 1499. (h) Nair, V.; Sethumadhavan, D.; Nair, S. M.; Shanmugam, P.; Treesa, P. M.; Eigendorf, G. K. Synthesis 2002, 1655. (i) Kozawa, Y.; Mori, M. Tetrahedron Lett. 2001, 42, 4869. (j) Kinderman, S. S.; van Maarseveen, J. H.; Schoemaker, H. E.; Hiemstra, H.; Rutjes, F. P. T., Org. Lett. 2001, 3, 2045. (k) van Boxtel, L. J.; Korbe, S.; Noltemeyer, M.; de Meijere, A. Eur. J. Org. Chem. 2001, 2283. (l) Grigg, R.; Köppen, I.; Rasparini, M.; Sridharan, V. Chem. Commun. 2001, 964. (m) For papers before 2001, see ref 5.
22. For recent allenamide chemistry, see: (a) Añorbe, L.; Poblador, A.; Domínguez, G.; Pérez-Castells, J. Tetrahedron Lett. 2004, 45, 4441. (b) Achmatowicz, M.; Hegedus, L. S. J. Org. Chem. 2004, 69, 2229. (c) Ranslow, P. D. B.; Hegedus, L. S.; de los Rios, C. J. Org. Chem. 2004, 69, 105. (d) Bacci, J. P.; Greenman, K. L.; Van Vranken, D. L. J. Org. Chem. 2003, 68, 4955. (e) Armstrong, A.; Cooke, R. S.; Shanahan, S. E. Org. Biomol. Chem. 2003, 1, 3142. (f) Gaul C.; Seebach, D. Helv. Chim. Acta 2002, 85, 963. (g) Kozawa, Y.; Mori, M. Tetrahedron Lett. 2002, 43, 1499. (h) Nair, V.; Sethumadhavan, D.; Nair, S. M.; Shanmugam, P.; Treesa, P. M.; Eigendorf, G. K. Synthesis 2002, 1655. (i) Kozawa, Y.; Mori, M. Tetrahedron Lett. 2001, 42, 4869. (j) Kinderman, S. S.; van Maarseveen, J. H.; Schoemaker, H. E.; Hiemstra, H.; Rutjes, F. P. T., Org. Lett. 2001, 3, 2045. (k) van Boxtel, L. J.; Korbe, S.; Noltemeyer, M.; de Meijere, A. Eur. J. Org. Chem. 2001, 2283. (l) Grigg, R.; Köppen, I.; Rasparini, M.; Sridharan, V. Chem. Commun. 2001, 964. (m) For papers before 2001, see ref 5.
23. For recent allenamide chemistry, see: (a) Añorbe, L.; Poblador, A.; Domínguez, G.; Pérez-Castells, J. Tetrahedron Lett. 2004, 45, 4441. (b) Achmatowicz, M.; Hegedus, L. S. J. Org. Chem. 2004, 69, 2229. (c) Ranslow, P. D. B.; Hegedus, L. S.; de los Rios, C. J. Org. Chem. 2004, 69, 105. (d) Bacci, J. P.; Greenman, K. L.; Van Vranken, D. L. J. Org. Chem. 2003, 68, 4955. (e) Armstrong, A.; Cooke, R. S.; Shanahan, S. E. Org. Biomol. Chem. 2003, 1, 3142. (f) Gaul C.; Seebach, D. Helv. Chim. Acta 2002, 85, 963. (g) Kozawa, Y.; Mori, M. Tetrahedron Lett. 2002, 43, 1499. (h) Nair, V.; Sethumadhavan, D.; Nair, S. M.; Shanmugam, P.; Treesa, P. M.; Eigendorf, G. K. Synthesis 2002, 1655. (i) Kozawa, Y.; Mori, M. Tetrahedron Lett. 2001, 42, 4869. (j) Kinderman, S. S.; van Maarseveen, J. H.; Schoemaker, H. E.; Hiemstra, H.; Rutjes, F. P. T., Org. Lett. 2001, 3, 2045. (k) van Boxtel, L. J.; Korbe, S.; Noltemeyer, M.; de Meijere, A. Eur. J. Org. Chem. 2001, 2283. (l) Grigg, R.; Köppen, I.; Rasparini, M.; Sridharan, V. Chem. Commun. 2001, 964. (m) For papers before 2001, see ref 5.
24. For recent allenamide chemistry, see: (a) Añorbe, L.; Poblador, A.; Domínguez, G.; Pérez-Castells, J. Tetrahedron Lett. 2004, 45, 4441. (b) Achmatowicz, M.; Hegedus, L. S. J. Org. Chem. 2004, 69, 2229. (c) Ranslow, P. D. B.; Hegedus, L. S.; de los Rios, C. J. Org. Chem. 2004, 69, 105. (d) Bacci, J. P.; Greenman, K. L.; Van Vranken, D. L. J. Org. Chem. 2003, 68, 4955. (e) Armstrong, A.; Cooke, R. S.; Shanahan, S. E. Org. Biomol. Chem. 2003, 1, 3142. (f) Gaul C.; Seebach, D. Helv. Chim. Acta 2002, 85, 963. (g) Kozawa, Y.; Mori, M. Tetrahedron Lett. 2002, 43, 1499. (h) Nair, V.; Sethumadhavan, D.; Nair, S. M.; Shanmugam, P.; Treesa, P. M.; Eigendorf, G. K. Synthesis 2002, 1655. (i) Kozawa, Y.; Mori, M. Tetrahedron Lett. 2001, 42, 4869. (j) Kinderman, S. S.; van Maarseveen, J. H.; Schoemaker, H. E.; Hiemstra, H.; Rutjes, F. P. T., Org. Lett. 2001, 3, 2045. (k) van Boxtel, L. J.; Korbe, S.; Noltemeyer, M.; de Meijere, A. Eur. J. Org. Chem. 2001, 2283. (l) Grigg, R.; Köppen, I.; Rasparini, M.; Sridharan, V. Chem. Commun. 2001, 964. (m) For papers before 2001, see ref 5.
25. For recent allenamide chemistry, see: (a) Añorbe, L.; Poblador, A.; Domínguez, G.; Pérez-Castells, J. Tetrahedron Lett. 2004, 45, 4441. (b) Achmatowicz, M.; Hegedus, L. S. J. Org. Chem. 2004, 69, 2229. (c) Ranslow, P. D. B.; Hegedus, L. S.; de los Rios, C. J. Org. Chem. 2004, 69, 105. (d) Bacci, J. P.; Greenman, K. L.; Van Vranken, D. L. J. Org. Chem. 2003, 68, 4955. (e) Armstrong, A.; Cooke, R. S.; Shanahan, S. E. Org. Biomol. Chem. 2003, 1, 3142. (f) Gaul C.; Seebach, D. Helv. Chim. Acta 2002, 85, 963. (g) Kozawa, Y.; Mori, M. Tetrahedron Lett. 2002, 43, 1499. (h) Nair, V.; Sethumadhavan, D.; Nair, S. M.; Shanmugam, P.; Treesa, P. M.; Eigendorf, G. K. Synthesis 2002, 1655. (i) Kozawa, Y.; Mori, M. Tetrahedron Lett. 2001, 42, 4869. (j) Kinderman, S. S.; van Maarseveen, J. H.; Schoemaker, H. E.; Hiemstra, H.; Rutjes, F. P. T., Org. Lett. 2001, 3, 2045. (k) van Boxtel, L. J.; Korbe, S.; Noltemeyer, M.; de Meijere, A. Eur. J. Org. Chem. 2001, 2283. (l) Grigg, R.; Köppen, I.; Rasparini, M.; Sridharan, V. Chem. Commun. 2001, 964. (m) For papers before 2001, see ref 5.
26. For recent allenamide chemistry, see: (a) Añorbe, L.; Poblador, A.; Domínguez, G.; Pérez-Castells, J. Tetrahedron Lett. 2004, 45, 4441. (b) Achmatowicz, M.; Hegedus, L. S. J. Org. Chem. 2004, 69, 2229. (c) Ranslow, P. D. B.; Hegedus, L. S.; de los Rios, C. J. Org. Chem. 2004, 69, 105. (d) Bacci, J. P.; Greenman, K. L.; Van Vranken, D. L. J. Org. Chem. 2003, 68, 4955. (e) Armstrong, A.; Cooke, R. S.; Shanahan, S. E. Org. Biomol. Chem. 2003, 1, 3142. (f) Gaul C.; Seebach, D. Helv. Chim. Acta 2002, 85, 963. (g) Kozawa, Y.; Mori, M. Tetrahedron Lett. 2002, 43, 1499. (h) Nair, V.; Sethumadhavan, D.; Nair, S. M.; Shanmugam, P.; Treesa, P. M.; Eigendorf, G. K. Synthesis 2002, 1655. (i) Kozawa, Y.; Mori, M. Tetrahedron Lett. 2001, 42, 4869. (j) Kinderman, S. S.; van Maarseveen, J. H.; Schoemaker, H. E.; Hiemstra, H.; Rutjes, F. P. T., Org. Lett. 2001, 3, 2045. (k) van Boxtel, L. J.; Korbe, S.; Noltemeyer, M.; de Meijere, A. Eur. J. Org. Chem. 2001, 2283. (l) Grigg, R.; Köppen, I.; Rasparini, M.; Sridharan, V. Chem. Commun. 2001, 964. (m) For papers before 2001, see ref 5.
27. For recent allenamide chemistry, see: (a) Añorbe, L.; Poblador, A.; Domínguez, G.; Pérez-Castells, J. Tetrahedron Lett. 2004, 45, 4441. (b) Achmatowicz, M.; Hegedus, L. S. J. Org. Chem. 2004, 69, 2229. (c) Ranslow, P. D. B.; Hegedus, L. S.; de los Rios, C. J. Org. Chem. 2004, 69, 105. (d) Bacci, J. P.; Greenman, K. L.; Van Vranken, D. L. J. Org. Chem. 2003, 68, 4955. (e) Armstrong, A.; Cooke, R. S.; Shanahan, S. E. Org. Biomol. Chem. 2003, 1, 3142. (f) Gaul C.; Seebach, D. Helv. Chim. Acta 2002, 85, 963. (g) Kozawa, Y.; Mori, M. Tetrahedron Lett. 2002, 43, 1499. (h) Nair, V.; Sethumadhavan, D.; Nair, S. M.; Shanmugam, P.; Treesa, P. M.; Eigendorf, G. K. Synthesis 2002, 1655. (i) Kozawa, Y.; Mori, M. Tetrahedron Lett. 2001, 42, 4869. (j) Kinderman, S. S.; van Maarseveen, J. H.; Schoemaker, H. E.; Hiemstra, H.; Rutjes, F. P. T., Org. Lett. 2001, 3, 2045. (k) van Boxtel, L. J.; Korbe, S.; Noltemeyer, M.; de Meijere, A. Eur. J. Org. Chem. 2001, 2283. (l) Grigg, R.; Köppen, I.; Rasparini, M.; Sridharan, V. Chem. Commun. 2001, 964. (m) For papers before 2001, see ref 5.
28. For our recent efforts, see: (a) Huang, J.; Hsung, R. P. J. Am. Chem. Soc. 2005, 127, 50. (b) Rameshkumar, C.; Hsung, R. P. Angew Chem., Int. Ed. 2004, 43, 615. (c) Berry, C. R.; Hsung, R. P. Tetrahedron 2004, 60, 7629. (d) Xiong, H.; Huang, J.; Ghosh, S.; Hsung, R. P. J. Am. Chem. Soc. 2003, 125, 12694. (e) Rameshkumar, C.; Hsung, R. P. Synlett 2003, 1241. (f) Berry, C. R.; Rameshkumar, C.; Tracey, M. R.; Wei, L.-L.; Hsung, R. P. Synlett 2003, 791. (g) Rameshkumar, C.; Xiong, H.; Tracey, M. R.; Berry, C. R.; Yao, L. J.; Hsung, R. P. J. Org. Chem. 2002, 67, 1339. (h) Xiong, H.; Hsung, R. P.; Berry, C. R.; Rameshkumar, C. J. Am. Chem. Soc. 2001, 123, 7174.
29. For our recent efforts, see: (a) Huang, J.; Hsung, R. P. J. Am. Chem. Soc. 2005, 127, 50. (b) Rameshkumar, C.; Hsung, R. P. Angew Chem., Int. Ed. 2004, 43, 615. (c) Berry, C. R.; Hsung, R. P. Tetrahedron 2004, 60, 7629. (d) Xiong, H.; Huang, J.; Ghosh, S.; Hsung, R. P. J. Am. Chem. Soc. 2003, 125, 12694. (e) Rameshkumar, C.; Hsung, R. P. Synlett 2003, 1241. (f) Berry, C. R.; Rameshkumar, C.; Tracey, M. R.; Wei, L.-L.; Hsung, R. P. Synlett 2003, 791. (g) Rameshkumar, C.; Xiong, H.; Tracey, M. R.; Berry, C. R.; Yao, L. J.; Hsung, R. P. J. Org. Chem. 2002, 67, 1339. (h) Xiong, H.; Hsung, R. P.; Berry, C. R.; Rameshkumar, C. J. Am. Chem. Soc. 2001, 123, 7174.
30. For our recent efforts, see: (a) Huang, J.; Hsung, R. P. J. Am. Chem. Soc. 2005, 127, 50. (b) Rameshkumar, C.; Hsung, R. P. Angew Chem., Int. Ed. 2004, 43, 615. (c) Berry, C. R.; Hsung, R. P. Tetrahedron 2004, 60, 7629. (d) Xiong, H.; Huang, J.; Ghosh, S.; Hsung, R. P. J. Am. Chem. Soc. 2003, 125, 12694. (e) Rameshkumar, C.; Hsung, R. P. Synlett 2003, 1241. (f) Berry, C. R.; Rameshkumar, C.; Tracey, M. R.; Wei, L.-L.; Hsung, R. P. Synlett 2003, 791. (g) Rameshkumar, C.; Xiong, H.; Tracey, M. R.; Berry, C. R.; Yao, L. J.; Hsung, R. P. J. Org. Chem. 2002, 67, 1339. (h) Xiong, H.; Hsung, R. P.; Berry, C. R.; Rameshkumar, C. J. Am. Chem. Soc. 2001, 123, 7174.
31. For our recent efforts, see: (a) Huang, J.; Hsung, R. P. J. Am. Chem. Soc. 2005, 127, 50. (b) Rameshkumar, C.; Hsung, R. P. Angew Chem., Int. Ed. 2004, 43, 615. (c) Berry, C. R.; Hsung, R. P. Tetrahedron 2004, 60, 7629. (d) Xiong, H.; Huang, J.; Ghosh, S.; Hsung, R. P. J. Am. Chem. Soc. 2003, 125, 12694. (e) Rameshkumar, C.; Hsung, R. P. Synlett 2003, 1241. (f) Berry, C. R.; Rameshkumar, C.; Tracey, M. R.; Wei, L.-L.; Hsung, R. P. Synlett 2003, 791. (g) Rameshkumar, C.; Xiong, H.; Tracey, M. R.; Berry, C. R.; Yao, L. J.; Hsung, R. P. J. Org. Chem. 2002, 67, 1339. (h) Xiong, H.; Hsung, R. P.; Berry, C. R.; Rameshkumar, C. J. Am. Chem. Soc. 2001, 123, 7174.
32. For our recent efforts, see: (a) Huang, J.; Hsung, R. P. J. Am. Chem. Soc. 2005, 127, 50. (b) Rameshkumar, C.; Hsung, R. P. Angew Chem., Int. Ed. 2004, 43, 615. (c) Berry, C. R.; Hsung, R. P. Tetrahedron 2004, 60, 7629. (d) Xiong, H.; Huang, J.; Ghosh, S.; Hsung, R. P. J. Am. Chem. Soc. 2003, 125, 12694. (e) Rameshkumar, C.; Hsung, R. P. Synlett 2003, 1241. (f) Berry, C. R.; Rameshkumar, C.; Tracey, M. R.; Wei, L.-L.; Hsung, R. P. Synlett 2003, 791. (g) Rameshkumar, C.; Xiong, H.; Tracey, M. R.; Berry, C. R.; Yao, L. J.; Hsung, R. P. J. Org. Chem. 2002, 67, 1339. (h) Xiong, H.; Hsung, R. P.; Berry, C. R.; Rameshkumar, C. J. Am. Chem. Soc. 2001, 123, 7174.
33. For our recent efforts, see: (a) Huang, J.; Hsung, R. P. J. Am. Chem. Soc. 2005, 127, 50. (b) Rameshkumar, C.; Hsung, R. P. Angew Chem., Int. Ed. 2004, 43, 615. (c) Berry, C. R.; Hsung, R. P. Tetrahedron 2004, 60, 7629. (d) Xiong, H.; Huang, J.; Ghosh, S.; Hsung, R. P. J. Am. Chem. Soc. 2003, 125, 12694. (e) Rameshkumar, C.; Hsung, R. P. Synlett 2003, 1241. (f) Berry, C. R.; Rameshkumar, C.; Tracey, M. R.; Wei, L.-L.; Hsung, R. P. Synlett 2003, 791. (g) Rameshkumar, C.; Xiong, H.; Tracey, M. R.; Berry, C. R.; Yao, L. J.; Hsung, R. P. J. Org. Chem. 2002, 67, 1339. (h) Xiong, H.; Hsung, R. P.; Berry, C. R.; Rameshkumar, C. J. Am. Chem. Soc. 2001, 123, 7174.
34. For our recent efforts, see: (a) Huang, J.; Hsung, R. P. J. Am. Chem. Soc. 2005, 127, 50. (b) Rameshkumar, C.; Hsung, R. P. Angew Chem., Int. Ed. 2004, 43, 615. (c) Berry, C. R.; Hsung, R. P. Tetrahedron 2004, 60, 7629. (d) Xiong, H.; Huang, J.; Ghosh, S.; Hsung, R. P. J. Am. Chem. Soc. 2003, 125, 12694. (e) Rameshkumar, C.; Hsung, R. P. Synlett 2003, 1241. (f) Berry, C. R.; Rameshkumar, C.; Tracey, M. R.; Wei, L.-L.; Hsung, R. P. Synlett 2003, 791. (g) Rameshkumar, C.; Xiong, H.; Tracey, M. R.; Berry, C. R.; Yao, L. J.; Hsung, R. P. J. Org. Chem. 2002, 67, 1339. (h) Xiong, H.; Hsung, R. P.; Berry, C. R.; Rameshkumar, C. J. Am. Chem. Soc. 2001, 123, 7174.
35. For our recent efforts, see: (a) Huang, J.; Hsung, R. P. J. Am. Chem. Soc. 2005, 127, 50. (b) Rameshkumar, C.; Hsung, R. P. Angew Chem., Int. Ed. 2004, 43, 615. (c) Berry, C. R.; Hsung, R. P. Tetrahedron 2004, 60, 7629. (d) Xiong, H.; Huang, J.; Ghosh, S.; Hsung, R. P. J. Am. Chem. Soc. 2003, 125, 12694. (e) Rameshkumar, C.; Hsung, R. P. Synlett 2003, 1241. (f) Berry, C. R.; Rameshkumar, C.; Tracey, M. R.; Wei, L.-L.; Hsung, R. P. Synlett 2003, 791. (g) Rameshkumar, C.; Xiong, H.; Tracey, M. R.; Berry, C. R.; Yao, L. J.; Hsung, R. P. J. Org. Chem. 2002, 67, 1339. (h) Xiong, H.; Hsung, R. P.; Berry, C. R.; Rameshkumar, C. J. Am. Chem. Soc. 2001, 123, 7174.
36. For leading references on Bergman cyclizations involving allenes, see: (a) Grissom, J. W.; Klingberg, D.; Huang, D.; Slattery, B. J. J. Org. Chem. 1997, 62, 603. (b) Grissom, J. W.; Huang, D. Angew. Chem., Int. Ed. Engl. 1995, 34, 2037. (c) Grissom, J. W.; Klingberg, D. Tetrahedron Lett. 1995, 36, 6607. (d) Grissom, J. W.; Huang, D. J. Org. Chem. 1994, 59, 5114.
37. For leading references on Bergman cyclizations involving allenes, see: (a) Grissom, J. W.; Klingberg, D.; Huang, D.; Slattery, B. J. J. Org. Chem. 1997, 62, 603. (b) Grissom, J. W.; Huang, D. Angew. Chem., Int. Ed. Engl. 1995, 34, 2037. (c) Grissom, J. W.; Klingberg, D. Tetrahedron Lett. 1995, 36, 6607. (d) Grissom, J. W.; Huang, D. J. Org. Chem. 1994, 59, 5114.
38. For leading references on Bergman cyclizations involving allenes, see: (a) Grissom, J. W.; Klingberg, D.; Huang, D.; Slattery, B. J. J. Org. Chem. 1997, 62, 603. (b) Grissom, J. W.; Huang, D. Angew. Chem., Int. Ed. Engl. 1995, 34, 2037. (c) Grissom, J. W.; Klingberg, D. Tetrahedron Lett. 1995, 36, 6607. (d) Grissom, J. W.; Huang, D. J. Org. Chem. 1994, 59, 5114.
39. For leading references on Bergman cyclizations involving allenes, see: (a) Grissom, J. W.; Klingberg, D.; Huang, D.; Slattery, B. J. J. Org. Chem. 1997, 62, 603. (b) Grissom, J. W.; Huang, D. Angew. Chem., Int. Ed. Engl. 1995, 34, 2037. (c) Grissom, J. W.; Klingberg, D. Tetrahedron Lett. 1995, 36, 6607. (d) Grissom, J. W.; Huang, D. J. Org. Chem. 1994, 59, 5114.
40. Also see: (a) Myers, A. G.; Dragovich, P. S. J. Am. Chem. Soc. 1989, 111, 9130. (b) Myers, A. G.; Kuo, E. Y.; Finney, N. S. J. Am. Chem. Soc. 1989, 111, 8057.
41. Also see: (a) Myers, A. G.; Dragovich, P. S. J. Am. Chem. Soc. 1989, 111, 9130. (b) Myers, A. G.; Kuo, E. Y.; Finney, N. S. J. Am. Chem. Soc. 1989, 111, 8057.
42. Wang, K. K.; Zhang, H.-R.; Petersen, J. L. J. Org. Chem. 1999, 64, 1650.
43. For other related references, see: (a) Schmittel, M.; Strittmatter, M.; Kiau, S. Tetrahedron Lett. 1995, 36, 4975. (b) Krause, N.; Hohmann, M. Synlett 1996, 89. (c) Gillmann, T.; Hülsen, T.; Massa, W.; Wocadlo, S. Synlett 1995, 1257.
44. For other related references, see: (a) Schmittel, M.; Strittmatter, M.; Kiau, S. Tetrahedron Lett. 1995, 36, 4975. (b) Krause, N.; Hohmann, M. Synlett 1996, 89. (c) Gillmann, T.; Hülsen, T.; Massa, W.; Wocadlo, S. Synlett 1995, 1257.
45. For other related references, see: (a) Schmittel, M.; Strittmatter, M.; Kiau, S. Tetrahedron Lett. 1995, 36, 4975. (b) Krause, N.; Hohmann, M. Synlett 1996, 89. (c) Gillmann, T.; Hülsen, T.; Massa, W.; Wocadlo, S. Synlett 1995, 1257.
46. D, and MS; see Supporting Information.
47. (a) Wei, L.-L.; Xiong, H.; Douglas, C. J.; Hsung, R. P. Tetrahedron Lett. 1999, 40, 6903.
48. (b) Hsung, R. P.; Zificsak, C. A.; Wei, L.-L.; Douglas, C. J.; Xiong, H.; Mulder, J. A. Org. Lett. 1999, 1, 1237.
49. (c) Wei, L.-L.; Mulder, J. A.; Xiong, H.; Zificsak, C. A.; Douglas, C. J.; Hsung, R. P. Tetrahedron 2001, 57, 459.
50. (d) Huang, J.; Xiong, H.; Hsung, R. P.; Rameshkumar, C.; Mulder, J. A.; Grebe, T. P. Org. Lett. 2002, 4, 2417.
51. 3SnH (1.5 equiv, 189.5 μL) was added dropwise via a syringe. [Note: a syringe pump was used for the tandem reaction.] The reaction was heated at 80°C for 3 h before being cooled to room temperature. A saturated aqueous KF solution (5 mL) was then added, and the mixture was stirred for another 2 h at room temperature. After filtration through Celite, the biphasic filtrate was extracted with 5 mL of EtOAc. The aqueous layer was extracted with another 5 mL portion of EtOAc after separation. The combined organic extracts were concentrated under reduced pressure, and the crude residue was purified using flash silica gel column chromatography (gradient eluent: 0-10% EtOAc in hexane) to provide 86.1 mg (75% yield) of compound 17a as thick yellow oil.
52. Xiong, H.; Hsung, R. P.; Wei, L.-L.; Berry, C. R.; Mulder, J. A.; Stockwell, B. Org. Lett. 2000, 2, 2869.
53. For a related diastereoselective example, see: Yamauchi, T.; Sugiyama, J.; Higashiyama, K. Heterocycles 2002, 58, 431.
54. Compounds 32 and 33 are not separable. Also found on occasions was the central-cyclized product as part of the inseparable mixture.
55. For a recent review on radical processes leading to bridged azabicycles, see: Sato, T.; Ikeda, M. Heterocycles 2003, 59, 429.