Structurally Novel Bi- and Tricyclic β-Lactams via [2 + 2] Cycloaddition or Radical Reactions in 2-Azetidinone-Tethered Enallenes and Allenynes

Organic Letters

Volumn 5, Issue 21, 2003, Pages 3795-3798

  Alcaide, Benito ^a   Almendros, Pedro ^b   Aragoncillo, Cristina ^a  

^a UNIVERSIDAD COMPLUTENSE DE MADRID   (Spain)

^b UNIVERSITY OF BIRMINGHAM   (United Kingdom)

Author keywords

[No Author keywords available]

Indexed keywords

2 AZETIDINONE DERIVATIVE; ALCOHOL DERIVATIVE; ALDEHYDE DERIVATIVE; ALKENE; ALKYNE DERIVATIVE; ALLENE DERIVATIVE; BETA LACTAM DERIVATIVE; CARBONYL DERIVATIVE; METAL;

AQUEOUS SOLUTION; ARTICLE; CHEMICAL BOND; CHEMICAL STRUCTURE; CYCLIZATION; CYCLOADDITION; RADICAL REACTION; STEREOCHEMISTRY;

EID: 0242628828     PISSN: 15237060     EISSN: None     Source Type: Journal    
DOI: 10.1021/ol034995c     Document Type: Article

References (72)

1. For selected reviews, see: (a) Setti, E. L.; Micetich, R. G. Curr. Med. Chem. 1998, 5, 101. (b) The Organic Chemistry of β-Lactams; Georg, G. I., Ed.; VCH: New York, 1993. (c) Neuhaus, F. C.; Georgeopapadakou, N. H. In Emerging Targets in Antibacterial and Antifungal Chemotherapy; Sutcliffe, J., Georgeopapadakou, N. H., Eds.; Chapman and Hall: New York, 1992.
2. For selected reviews, see: (a) Setti, E. L.; Micetich, R. G. Curr. Med. Chem. 1998, 5, 101. (b) The Organic Chemistry of β-Lactams; Georg, G. I., Ed.; VCH: New York, 1993. (c) Neuhaus, F. C.; Georgeopapadakou, N. H. In Emerging Targets in Antibacterial and Antifungal Chemotherapy; Sutcliffe, J., Georgeopapadakou, N. H., Eds.; Chapman and Hall: New York, 1992.
3. For selected reviews, see: (a) Setti, E. L.; Micetich, R. G. Curr. Med. Chem. 1998, 5, 101. (b) The Organic Chemistry of β-Lactams; Georg, G. I., Ed.; VCH: New York, 1993. (c) Neuhaus, F. C.; Georgeopapadakou, N. H. In Emerging Targets in Antibacterial and Antifungal Chemotherapy; Sutcliffe, J., Georgeopapadakou, N. H., Eds.; Chapman and Hall: New York, 1992.
4. β-Lactamase enzymes catalyze the hydrolysis of β-lactams to give ring-opened β-amino acids that are no longer effective as inhibitors against their targets: bacterial membrane-bound transpeptidases enzymes. See, for example: (a) Sandanayaka, V. P.; Prashad, A. S. Curr. Med. Chem. 2002, 9, 1145. (b) Ritter, T. K.; Wong, C.-H. Angew. Chem., Int. Ed. 2001, 40, 3508. (c) Díaz, N.; Suárez, D.; Merz, K. M. M., Jr. J. Am. Chem. Soc. 2000, 122, 4197. (d) Page, M. I. Chem. Commun. 1998, 1609. (e) Niccolai, D.; Tarsi, L.; Thomas, R. J. Chem. Commun. 1997, 2333. (f) Hook, V. Chemistry in Britain 1997, 33, 34. (g) Spratt, B. G. Science 1994, 264, 388. (h) Davies, J. Science 1994, 264, 375.
5. β-Lactamase enzymes catalyze the hydrolysis of β-lactams to give ring-opened β-amino acids that are no longer effective as inhibitors against their targets: bacterial membrane-bound transpeptidases enzymes. See, for example: (a) Sandanayaka, V. P.; Prashad, A. S. Curr. Med. Chem. 2002, 9, 1145. (b) Ritter, T. K.; Wong, C.-H. Angew. Chem., Int. Ed. 2001, 40, 3508. (c) Díaz, N.; Suárez, D.; Merz, K. M. M., Jr. J. Am. Chem. Soc. 2000, 122, 4197. (d) Page, M. I. Chem. Commun. 1998, 1609. (e) Niccolai, D.; Tarsi, L.; Thomas, R. J. Chem. Commun. 1997, 2333. (f) Hook, V. Chemistry in Britain 1997, 33, 34. (g) Spratt, B. G. Science 1994, 264, 388. (h) Davies, J. Science 1994, 264, 375.
6. β-Lactamase enzymes catalyze the hydrolysis of β-lactams to give ring-opened β-amino acids that are no longer effective as inhibitors against their targets: bacterial membrane-bound transpeptidases enzymes. See, for example: (a) Sandanayaka, V. P.; Prashad, A. S. Curr. Med. Chem. 2002, 9, 1145. (b) Ritter, T. K.; Wong, C.-H. Angew. Chem., Int. Ed. 2001, 40, 3508. (c) Díaz, N.; Suárez, D.; Merz, K. M. M., Jr. J. Am. Chem. Soc. 2000, 122, 4197. (d) Page, M. I. Chem. Commun. 1998, 1609. (e) Niccolai, D.; Tarsi, L.; Thomas, R. J. Chem. Commun. 1997, 2333. (f) Hook, V. Chemistry in Britain 1997, 33, 34. (g) Spratt, B. G. Science 1994, 264, 388. (h) Davies, J. Science 1994, 264, 375.
7. β-Lactamase enzymes catalyze the hydrolysis of β-lactams to give ring-opened β-amino acids that are no longer effective as inhibitors against their targets: bacterial membrane-bound transpeptidases enzymes. See, for example: (a) Sandanayaka, V. P.; Prashad, A. S. Curr. Med. Chem. 2002, 9, 1145. (b) Ritter, T. K.; Wong, C.-H. Angew. Chem., Int. Ed. 2001, 40, 3508. (c) Díaz, N.; Suárez, D.; Merz, K. M. M., Jr. J. Am. Chem. Soc. 2000, 122, 4197. (d) Page, M. I. Chem. Commun. 1998, 1609. (e) Niccolai, D.; Tarsi, L.; Thomas, R. J. Chem. Commun. 1997, 2333. (f) Hook, V. Chemistry in Britain 1997, 33, 34. (g) Spratt, B. G. Science 1994, 264, 388. (h) Davies, J. Science 1994, 264, 375.
8. β-Lactamase enzymes catalyze the hydrolysis of β-lactams to give ring-opened β-amino acids that are no longer effective as inhibitors against their targets: bacterial membrane-bound transpeptidases enzymes. See, for example: (a) Sandanayaka, V. P.; Prashad, A. S. Curr. Med. Chem. 2002, 9, 1145. (b) Ritter, T. K.; Wong, C.-H. Angew. Chem., Int. Ed. 2001, 40, 3508. (c) Díaz, N.; Suárez, D.; Merz, K. M. M., Jr. J. Am. Chem. Soc. 2000, 122, 4197. (d) Page, M. I. Chem. Commun. 1998, 1609. (e) Niccolai, D.; Tarsi, L.; Thomas, R. J. Chem. Commun. 1997, 2333. (f) Hook, V. Chemistry in Britain 1997, 33, 34. (g) Spratt, B. G. Science 1994, 264, 388. (h) Davies, J. Science 1994, 264, 375.
9. β-Lactamase enzymes catalyze the hydrolysis of β-lactams to give ring-opened β-amino acids that are no longer effective as inhibitors against their targets: bacterial membrane-bound transpeptidases enzymes. See, for example: (a) Sandanayaka, V. P.; Prashad, A. S. Curr. Med. Chem. 2002, 9, 1145. (b) Ritter, T. K.; Wong, C.-H. Angew. Chem., Int. Ed. 2001, 40, 3508. (c) Díaz, N.; Suárez, D.; Merz, K. M. M., Jr. J. Am. Chem. Soc. 2000, 122, 4197. (d) Page, M. I. Chem. Commun. 1998, 1609. (e) Niccolai, D.; Tarsi, L.; Thomas, R. J. Chem. Commun. 1997, 2333. (f) Hook, V. Chemistry in Britain 1997, 33, 34. (g) Spratt, B. G. Science 1994, 264, 388. (h) Davies, J. Science 1994, 264, 375.
10. β-Lactamase enzymes catalyze the hydrolysis of β-lactams to give ring-opened β-amino acids that are no longer effective as inhibitors against their targets: bacterial membrane-bound transpeptidases enzymes. See, for example: (a) Sandanayaka, V. P.; Prashad, A. S. Curr. Med. Chem. 2002, 9, 1145. (b) Ritter, T. K.; Wong, C.-H. Angew. Chem., Int. Ed. 2001, 40, 3508. (c) Díaz, N.; Suárez, D.; Merz, K. M. M., Jr. J. Am. Chem. Soc. 2000, 122, 4197. (d) Page, M. I. Chem. Commun. 1998, 1609. (e) Niccolai, D.; Tarsi, L.; Thomas, R. J. Chem. Commun. 1997, 2333. (f) Hook, V. Chemistry in Britain 1997, 33, 34. (g) Spratt, B. G. Science 1994, 264, 388. (h) Davies, J. Science 1994, 264, 375.
11. β-Lactamase enzymes catalyze the hydrolysis of β-lactams to give ring-opened β-amino acids that are no longer effective as inhibitors against their targets: bacterial membrane-bound transpeptidases enzymes. See, for example: (a) Sandanayaka, V. P.; Prashad, A. S. Curr. Med. Chem. 2002, 9, 1145. (b) Ritter, T. K.; Wong, C.-H. Angew. Chem., Int. Ed. 2001, 40, 3508. (c) Díaz, N.; Suárez, D.; Merz, K. M. M., Jr. J. Am. Chem. Soc. 2000, 122, 4197. (d) Page, M. I. Chem. Commun. 1998, 1609. (e) Niccolai, D.; Tarsi, L.; Thomas, R. J. Chem. Commun. 1997, 2333. (f) Hook, V. Chemistry in Britain 1997, 33, 34. (g) Spratt, B. G. Science 1994, 264, 388. (h) Davies, J. Science 1994, 264, 375.
12. For selected references, see: (a) Kanno, O.; Kawamoto, I. Tetrahedron 2000, 56, 5639. (b) Hanessian, S.; Reddy, B. Tetrahedron 1999, 55, 3427. (c) Biondi, S.; Pecunioso, A.; Busi, F.; Contini, S. A.; Donati, D.; Maffeis, M.; Pizzi, D. A.; Rossi, L.; Rossi, T.; Sabbatine, F. M. Tetrahedron 2000, 56, 5649. (d) Ghiron, C.; Rossi, T. The Chemistry of Trinems in Targets in Heterocyclic Systems - Chemistry and Properties; Attanasi, O. A., Spinelli, D., Eds.; Societa Chimica Italiana: Rome, 1997; Vol. 1, pp 161-186. (e) Ngo, J.; Castañer, J. Drugs Future 1996, 21, 1238.
13. For selected references, see: (a) Kanno, O.; Kawamoto, I. Tetrahedron 2000, 56, 5639. (b) Hanessian, S.; Reddy, B. Tetrahedron 1999, 55, 3427. (c) Biondi, S.; Pecunioso, A.; Busi, F.; Contini, S. A.; Donati, D.; Maffeis, M.; Pizzi, D. A.; Rossi, L.; Rossi, T.; Sabbatine, F. M. Tetrahedron 2000, 56, 5649. (d) Ghiron, C.; Rossi, T. The Chemistry of Trinems in Targets in Heterocyclic Systems - Chemistry and Properties; Attanasi, O. A., Spinelli, D., Eds.; Societa Chimica Italiana: Rome, 1997; Vol. 1, pp 161-186. (e) Ngo, J.; Castañer, J. Drugs Future 1996, 21, 1238.
14. For selected references, see: (a) Kanno, O.; Kawamoto, I. Tetrahedron 2000, 56, 5639. (b) Hanessian, S.; Reddy, B. Tetrahedron 1999, 55, 3427. (c) Biondi, S.; Pecunioso, A.; Busi, F.; Contini, S. A.; Donati, D.; Maffeis, M.; Pizzi, D. A.; Rossi, L.; Rossi, T.; Sabbatine, F. M. Tetrahedron 2000, 56, 5649. (d) Ghiron, C.; Rossi, T. The Chemistry of Trinems in Targets in Heterocyclic Systems - Chemistry and Properties; Attanasi, O. A., Spinelli, D., Eds.; Societa Chimica Italiana: Rome, 1997; Vol. 1, pp 161-186. (e) Ngo, J.; Castañer, J. Drugs Future 1996, 21, 1238.
15. For selected references, see: (a) Kanno, O.; Kawamoto, I. Tetrahedron 2000, 56, 5639. (b) Hanessian, S.; Reddy, B. Tetrahedron 1999, 55, 3427. (c) Biondi, S.; Pecunioso, A.; Busi, F.; Contini, S. A.; Donati, D.; Maffeis, M.; Pizzi, D. A.; Rossi, L.; Rossi, T.; Sabbatine, F. M. Tetrahedron 2000, 56, 5649. (d) Ghiron, C.; Rossi, T. The Chemistry of Trinems in Targets in Heterocyclic Systems - Chemistry and Properties; Attanasi, O. A., Spinelli, D., Eds.; Societa Chimica Italiana: Rome, 1997; Vol. 1, pp 161-186. (e) Ngo, J.; Castañer, J. Drugs Future 1996, 21, 1238.
16. For selected references, see: (a) Kanno, O.; Kawamoto, I. Tetrahedron 2000, 56, 5639. (b) Hanessian, S.; Reddy, B. Tetrahedron 1999, 55, 3427. (c) Biondi, S.; Pecunioso, A.; Busi, F.; Contini, S. A.; Donati, D.; Maffeis, M.; Pizzi, D. A.; Rossi, L.; Rossi, T.; Sabbatine, F. M. Tetrahedron 2000, 56, 5649. (d) Ghiron, C.; Rossi, T. The Chemistry of Trinems in Targets in Heterocyclic Systems - Chemistry and Properties; Attanasi, O. A., Spinelli, D., Eds.; Societa Chimica Italiana: Rome, 1997; Vol. 1, pp 161-186. (e) Ngo, J.; Castañer, J. Drugs Future 1996, 21, 1238.
17. Some of the more notable advances concern the development of mechanism-based serine protease inhibitors of elastase, cytomegalovirus, protease, thrombin, and prostate-specific antigen. For selected examples, see: (a) Page, M. I.; Laws, A. P. Tetrahedron 2000, 56, 5631. (b) Haley, T. M.; Angier, S. J.; Borthwick, A. D.; Singh, R.; Micetich, R. G. Drugs 2000, 3, 512. (c) Bonneau, P. R.; Hasani, F.; Plouffe, C.; Malenfant, E.; LaPlante, S. R.; Guse, I.; Ogilvie, W. W.; Plante, R.; Davidson, W. C.; Hopkins, J. L.; Morelock, M. M.; Cordingley, M. G.; Deziel, R. J. Am. Chem. Soc. 1999, 121, 2965. (d) Ogilvie, W. W.; Yoakim, C.; Do, F.; Hache, B.; Lagace, L.; Naud, J.; O'Meara, J. A.; Deziel, R. Bioorg. Med. Chem. Lett. 1999, 9, 1521. (e) Vaccaro, W. D.; Davis, H. R., Jr. Bioorg. Med. Chem. Lett. 1998, 8, 313. (f) Borthwick, A. D.; Weingarte, G.; Haley, T. M.; Tomaszewski, M.; Wang, W.; Hu, Z.; Bedard, J.; Jin, H.; Yuen, L.; Mansour, T. S. Bioorg. Med. Chem. Lett. 1998, 8, 365. (g) Han, W. T.; Trehan, A. K.; Wright, J. J. K.; Federici, M. E.; Seiler, S. M.; Meanwell, N. A. Bioorg. Med. Chem. 1995, 3, 1123.
18. Some of the more notable advances concern the development of mechanism-based serine protease inhibitors of elastase, cytomegalovirus, protease, thrombin, and prostate-specific antigen. For selected examples, see: (a) Page, M. I.; Laws, A. P. Tetrahedron 2000, 56, 5631. (b) Haley, T. M.; Angier, S. J.; Borthwick, A. D.; Singh, R.; Micetich, R. G. Drugs 2000, 3, 512. (c) Bonneau, P. R.; Hasani, F.; Plouffe, C.; Malenfant, E.; LaPlante, S. R.; Guse, I.; Ogilvie, W. W.; Plante, R.; Davidson, W. C.; Hopkins, J. L.; Morelock, M. M.; Cordingley, M. G.; Deziel, R. J. Am. Chem. Soc. 1999, 121, 2965. (d)Ogilvie, W. W.; Yoakim, C.; Do, F.; Hache, B.; Lagace, L.; Naud, J.; O'Meara, J. A.; Deziel, R. Bioorg. Med. Chem. Lett. 1999, 9, 1521. (e) Vaccaro, W. D.; Davis, H. R., Jr. Bioorg. Med. Chem. Lett. 1998, 8, 313. (f) Borthwick, A. D.; Weingarte, G.; Haley, T. M.; Tomaszewski, M.; Wang, W.; Hu, Z.; Bedard, J.; Jin, H.; Yuen, L.; Mansour, T. S. Bioorg. Med. Chem. Lett. 1998, 8, 365. (g) Han, W. T.; Trehan, A. K.; Wright, J. J. K.; Federici, M. E.; Seiler, S. M.; Meanwell, N. A. Bioorg. Med. Chem. 1995, 3, 1123.
19. Some of the more notable advances concern the development of mechanism-based serine protease inhibitors of elastase, cytomegalovirus, protease, thrombin, and prostate-specific antigen. For selected examples, see: (a) Page, M. I.; Laws, A. P. Tetrahedron 2000, 56, 5631. (b) Haley, T. M.; Angier, S. J.; Borthwick, A. D.; Singh, R.; Micetich, R. G. Drugs 2000, 3, 512. (c) Bonneau, P. R.; Hasani, F.; Plouffe, C.; Malenfant, E.; LaPlante, S. R.; Guse, I.; Ogilvie, W. W.; Plante, R.; Davidson, W. C.; Hopkins, J. L.; Morelock, M. M.; Cordingley, M. G.; Deziel, R. J. Am. Chem. Soc. 1999, 121, 2965. (d) Ogilvie, W. W.; Yoakim, C.; Do, F.; Hache, B.; Lagace, L.; Naud, J.; O'Meara, J. A.; Deziel, R. Bioorg. Med. Chem. Lett. 1999, 9, 1521. (e) Vaccaro, W. D.; Davis, H. R., Jr. Bioorg. Med. Chem. Lett. 1998, 8, 313. (f) Borthwick, A. D.; Weingarte, G.; Haley, T. M.; Tomaszewski, M.; Wang, W.; Hu, Z.; Bedard, J.; Jin, H.; Yuen, L.; Mansour, T. S. Bioorg. Med. Chem. Lett. 1998, 8, 365. (g) Han, W. T.; Trehan, A. K.; Wright, J. J. K.; Federici, M. E.; Seiler, S. M.; Meanwell, N. A. Bioorg. Med. Chem. 1995, 3, 1123.
20. Some of the more notable advances concern the development of mechanism-based serine protease inhibitors of elastase, cytomegalovirus, protease, thrombin, and prostate-specific antigen. For selected examples, see: (a) Page, M. I.; Laws, A. P. Tetrahedron 2000, 56, 5631. (b) Haley, T. M.; Angier, S. J.; Borthwick, A. D.; Singh, R.; Micetich, R. G. Drugs 2000, 3, 512. (c) Bonneau, P. R.; Hasani, F.; Plouffe, C.; Malenfant, E.; LaPlante, S. R.; Guse, I.; Ogilvie, W. W.; Plante, R.; Davidson, W. C.; Hopkins, J. L.; Morelock, M. M.; Cordingley, M. G.; Deziel, R. J. Am. Chem. Soc. 1999, 121, 2965. (d) Ogilvie, W. W.; Yoakim, C.; Do, F.; Hache, B.; Lagace, L.; Naud, J.; O'Meara, J. A.; Deziel, R. Bioorg. Med. Chem. Lett. 1999, 9, 1521. (e) Vaccaro, W. D.; Davis, H. R., Jr. Bioorg. Med. Chem. Lett. 1998, 8, 313. (f) Borthwick, A. D.; Weingarte, G.; Haley, T. M.; Tomaszewski, M.; Wang, W.; Hu, Z.; Bedard, J.; Jin, H.; Yuen, L.; Mansour, T. S. Bioorg. Med. Chem. Lett. 1998, 8, 365. (g) Han, W. T.; Trehan, A. K.; Wright, J. J. K.; Federici, M. E.; Seiler, S. M.; Meanwell, N. A. Bioorg. Med. Chem. 1995, 3, 1123.
21. Some of the more notable advances concern the development of mechanism-based serine protease inhibitors of elastase, cytomegalovirus, protease, thrombin, and prostate-specific antigen. For selected examples, see: (a) Page, M. I.; Laws, A. P. Tetrahedron 2000, 56, 5631. (b) Haley, T. M.; Angier, S. J.; Borthwick, A. D.; Singh, R.; Micetich, R. G. Drugs 2000, 3, 512. (c) Bonneau, P. R.; Hasani, F.; Plouffe, C.; Malenfant, E.; LaPlante, S. R.; Guse, I.; Ogilvie, W. W.; Plante, R.; Davidson, W. C.; Hopkins, J. L.; Morelock, M. M.; Cordingley, M. G.; Deziel, R. J. Am. Chem. Soc. 1999, 121, 2965. (d) Ogilvie, W. W.; Yoakim, C.; Do, F.; Hache, B.; Lagace, L.; Naud, J.; O'Meara, J. A.; Deziel, R. Bioorg. Med. Chem. Lett. 1999, 9, 1521. (e) Vaccaro, W. D.; Davis, H. R., Jr. Bioorg. Med. Chem. Lett. 1998, 8, 313. (f) Borthwick, A. D.; Weingarte, G.; Haley, T. M.; Tomaszewski, M.; Wang, W.; Hu, Z.; Bedard, J.; Jin, H.; Yuen, L.; Mansour, T. S. Bioorg. Med. Chem. Lett. 1998, 8, 365. (g) Han, W. T.; Trehan, A. K.; Wright, J. J. K.; Federici, M. E.; Seiler, S. M.; Meanwell, N. A. Bioorg. Med. Chem. 1995, 3, 1123.
22. Some of the more notable advances concern the development of mechanism-based serine protease inhibitors of elastase, cytomegalovirus, protease, thrombin, and prostate-specific antigen. For selected examples, see: (a) Page, M. I.; Laws, A. P. Tetrahedron 2000, 56, 5631. (b) Haley, T. M.; Angier, S. J.; Borthwick, A. D.; Singh, R.; Micetich, R. G. Drugs 2000, 3, 512. (c) Bonneau, P. R.; Hasani, F.; Plouffe, C.; Malenfant, E.; LaPlante, S. R.; Guse, I.; Ogilvie, W. W.; Plante, R.; Davidson, W. C.; Hopkins, J. L.; Morelock, M. M.; Cordingley, M. G.; Deziel, R. J. Am. Chem. Soc. 1999, 121, 2965. (d) Ogilvie, W. W.; Yoakim, C.; Do, F.; Hache, B.; Lagace, L.; Naud, J.; O'Meara, J. A.; Deziel, R. Bioorg. Med. Chem. Lett. 1999, 9, 1521. (e) Vaccaro, W. D.; Davis, H. R., Jr. Bioorg. Med. Chem. Lett. 1998, 8, 313. (f) Borthwick, A. D.; Weingarte, G.; Haley, T. M.; Tomaszewski, M.; Wang, W.; Hu, Z.; Bedard, J.; Jin, H.; Yuen, L.; Mansour, T. S. Bioorg. Med. Chem. Lett. 1998, 8, 365. (g) Han, W. T.; Trehan, A. K.; Wright, J. J. K.; Federici, M. E.; Seiler, S. M.; Meanwell, N. A. Bioorg. Med. Chem. 1995, 3, 1123.
23. Some of the more notable advances concern the development of mechanism-based serine protease inhibitors of elastase, cytomegalovirus, protease, thrombin, and prostate-specific antigen. For selected examples, see: (a) Page, M. I.; Laws, A. P. Tetrahedron 2000, 56, 5631. (b) Haley, T. M.; Angier, S. J.; Borthwick, A. D.; Singh, R.; Micetich, R. G. Drugs 2000, 3, 512. (c) Bonneau, P. R.; Hasani, F.; Plouffe, C.; Malenfant, E.; LaPlante, S. R.; Guse, I.; Ogilvie, W. W.; Plante, R.; Davidson, W. C.; Hopkins, J. L.; Morelock, M. M.; Cordingley, M. G.; Deziel, R. J. Am. Chem. Soc. 1999, 121, 2965. (d) Ogilvie, W. W.; Yoakim, C.; Do, F.; Hache, B.; Lagace, L.; Naud, J.; O'Meara, J. A.; Deziel, R. Bioorg. Med. Chem. Lett. 1999, 9, 1521. (e) Vaccaro, W. D.; Davis, H. R., Jr. Bioorg. Med. Chem. Lett. 1998, 8, 313. (f) Borthwick, A. D.; Weingarte, G.; Haley, T. M.; Tomaszewski, M.; Wang, W.; Hu, Z.; Bedard, J.; Jin, H.; Yuen, L.; Mansour, T. S. Bioorg. Med. Chem. Lett. 1998, 8, 365. (g) Han, W. T.; Trehan, A. K.; Wright, J. J. K.; Federici, M. E.; Seiler, S. M.; Meanwell, N. A. Bioorg. Med. Chem. 1995, 3, 1123.
24. For reviews, see: (a) Alcaide, B.; Almendros, P. Synlett 2002, 381. (b) Alcaide, B.; Almendros, P. Chem. Soc. Rev. 2001, 30, 226. (c) Alcaide, B.; Almendros, P. Org. Prep. Proced. Int. 2001, 33, 315. (d) Palomo, C.; Aizpurua, J. M.; Ganboa, I.; Oiarbide, M. Synlett 2001, 1813. (e) Palomo, C.; Aizpurua, J. M.; Ganboa, I.; Oiarbide, M. Amino Acids 1999, 16, 321. (f) Ojima, I.; Delaloge, F. Chem. Soc. Rev. 1997, 26, 377. (g) Ojima, I. Adv. Asym. Synth. 1995, 1, 95. (h) Manhas, M. S.; Wagle, D. R.; Chiang, J.; Bose, A. K. Heterocycles 1988, 27, 1755.
25. For reviews, see: (a) Alcaide, B.; Almendros, P. Synlett 2002, 381. (b) Alcaide, B.; Almendros, P. Chem. Soc. Rev. 2001, 30, 226. (c) Alcaide, B.; Almendros, P. Org. Prep. Proced. Int. 2001, 33, 315. (d) Palomo, C.; Aizpurua, J. M.; Ganboa, I.; Oiarbide, M. Synlett 2001, 1813. (e) Palomo, C.; Aizpurua, J. M.; Ganboa, I.; Oiarbide, M. Amino Acids 1999, 16, 321. (f) Ojima, I.; Delaloge, F. Chem. Soc. Rev. 1997, 26, 377. (g) Ojima, I. Adv. Asym. Synth. 1995, 1, 95. (h) Manhas, M. S.; Wagle, D. R.; Chiang, J.; Bose, A. K. Heterocycles 1988, 27, 1755.
26. For reviews, see: (a) Alcaide, B.; Almendros, P. Synlett 2002, 381. (b) Alcaide, B.; Almendros, P. Chem. Soc. Rev. 2001, 30, 226. (c) Alcaide, B.; Almendros, P. Org. Prep. Proced. Int. 2001, 33, 315. (d) Palomo, C.; Aizpurua, J. M.; Ganboa, I.; Oiarbide, M. Synlett 2001, 1813. (e) Palomo, C.; Aizpurua, J. M.; Ganboa, I.; Oiarbide, M. Amino Acids 1999, 16, 321. (f) Ojima, I.; Delaloge, F. Chem. Soc. Rev. 1997, 26, 377. (g) Ojima, I. Adv. Asym. Synth. 1995, 1, 95. (h) Manhas, M. S.; Wagle, D. R.; Chiang, J.; Bose, A. K. Heterocycles 1988, 27, 1755.
27. For reviews, see: (a) Alcaide, B.; Almendros, P. Synlett 2002, 381. (b) Alcaide, B.; Almendros, P. Chem. Soc. Rev. 2001, 30, 226. (c) Alcaide, B.; Almendros, P. Org. Prep. Proced. Int. 2001, 33, 315. (d) Palomo, C.; Aizpurua, J. M.; Ganboa, I.; Oiarbide, M. Synlett 2001, 1813. (e) Palomo, C.; Aizpurua, J. M.; Ganboa, I.; Oiarbide, M. Amino Acids 1999, 16, 321. (f) Ojima, I.; Delaloge, F. Chem. Soc. Rev. 1997, 26, 377. (g) Ojima, I. Adv. Asym. Synth. 1995, 1, 95. (h) Manhas, M. S.; Wagle, D. R.; Chiang, J.; Bose, A. K. Heterocycles 1988, 27, 1755.
28. For reviews, see: (a) Alcaide, B.; Almendros, P. Synlett 2002, 381. (b) Alcaide, B.; Almendros, P. Chem. Soc. Rev. 2001, 30, 226. (c) Alcaide, B.; Almendros, P. Org. Prep. Proced. Int. 2001, 33, 315. (d) Palomo, C.; Aizpurua, J. M.; Ganboa, I.; Oiarbide, M. Synlett 2001, 1813. (e) Palomo, C.; Aizpurua, J. M.; Ganboa, I.; Oiarbide, M. Amino Acids 1999, 16, 321. (f) Ojima, I.; Delaloge, F. Chem. Soc. Rev. 1997, 26, 377. (g) Ojima, I. Adv. Asym. Synth. 1995, 1, 95. (h) Manhas, M. S.; Wagle, D. R.; Chiang, J.; Bose, A. K. Heterocycles 1988, 27, 1755.
29. For reviews, see: (a) Alcaide, B.; Almendros, P. Synlett 2002, 381. (b) Alcaide, B.; Almendros, P. Chem. Soc. Rev. 2001, 30, 226. (c) Alcaide, B.; Almendros, P. Org. Prep. Proced. Int. 2001, 33, 315. (d) Palomo, C.; Aizpurua, J. M.; Ganboa, I.; Oiarbide, M. Synlett 2001, 1813. (e) Palomo, C.; Aizpurua, J. M.; Ganboa, I.; Oiarbide, M. Amino Acids 1999, 16, 321. (f) Ojima, I.; Delaloge, F. Chem. Soc. Rev. 1997, 26, 377. (g) Ojima, I. Adv. Asym. Synth. 1995, 1, 95. (h) Manhas, M. S.; Wagle, D. R.; Chiang, J.; Bose, A. K. Heterocycles 1988, 27, 1755.
30. For reviews, see: (a) Alcaide, B.; Almendros, P. Synlett 2002, 381. (b) Alcaide, B.; Almendros, P. Chem. Soc. Rev. 2001, 30, 226. (c) Alcaide, B.; Almendros, P. Org. Prep. Proced. Int. 2001, 33, 315. (d) Palomo, C.; Aizpurua, J. M.; Ganboa, I.; Oiarbide, M. Synlett 2001, 1813. (e) Palomo, C.; Aizpurua, J. M.; Ganboa, I.; Oiarbide, M. Amino Acids 1999, 16, 321. (f) Ojima, I.; Delaloge, F. Chem. Soc. Rev. 1997, 26, 377. (g) Ojima, I. Adv. Asym. Synth. 1995, 1, 95. (h) Manhas, M. S.; Wagle, D. R.; Chiang, J.; Bose, A. K. Heterocycles 1988, 27, 1755.
31. For reviews, see: (a) Alcaide, B.; Almendros, P. Synlett 2002, 381. (b) Alcaide, B.; Almendros, P. Chem. Soc. Rev. 2001, 30, 226. (c) Alcaide, B.; Almendros, P. Org. Prep. Proced. Int. 2001, 33, 315. (d) Palomo, C.; Aizpurua, J. M.; Ganboa, I.; Oiarbide, M. Synlett 2001, 1813. (e) Palomo, C.; Aizpurua, J. M.; Ganboa, I.; Oiarbide, M. Amino Acids 1999, 16, 321. (f) Ojima, I.; Delaloge, F. Chem. Soc. Rev. 1997, 26, 377. (g) Ojima, I. Adv. Asym. Synth. 1995, 1, 95. (h) Manhas, M. S.; Wagle, D. R.; Chiang, J.; Bose, A. K. Heterocycles 1988, 27, 1755.
32. For a recent review on bi- and tricyclic-β-lactams with nonclassical structures, see: Alcaide, B.; Almendros, P. Curr. Org. Chem. 2002, 6, 245.
33. For general reviews, see: (a) Patai, S. In The Chemistry of Ketenes, Allenes, and Related Compounds; Wiley: Chichester, 1980. (b) Schuster, H. F.; Coppola, G. M. In Allenes in Organic Synthesis; Wiley: New York, 1984. (c) Landor, S. R. The Chemistry of the Allenes; Academic Press: New York, 1982. (d) Lu, X.; Zhang, C.; Xu, Z. Acc. Chem. Res. 2001, 34, 535.
34. For general reviews, see: (a) Patai, S. In The Chemistry of Ketenes, Allenes, and Related Compounds; Wiley: Chichester, 1980. (b) Schuster, H. F.; Coppola, G. M. In Allenes in Organic Synthesis; Wiley: New York, 1984. (c) Landor, S. R. The Chemistry of the Allenes; Academic Press: New York, 1982. (d) Lu, X.; Zhang, C.; Xu, Z. Acc. Chem. Res. 2001, 34, 535.
35. For general reviews, see: (a) Patai, S. In The Chemistry of Ketenes, Allenes, and Related Compounds; Wiley: Chichester, 1980. (b) Schuster, H. F.; Coppola, G. M. In Allenes in Organic Synthesis; Wiley: New York, 1984. (c) Landor, S. R. The Chemistry of the Allenes; Academic Press: New York, 1982. (d) Lu, X.; Zhang, C.; Xu, Z. Acc. Chem. Res. 2001, 34, 535.
36. For general reviews, see: (a) Patai, S. In The Chemistry of Ketenes, Allenes, and Related Compounds; Wiley: Chichester, 1980. (b) Schuster, H. F.; Coppola, G. M. In Allenes in Organic Synthesis; Wiley: New York, 1984. (c) Landor, S. R. The Chemistry of the Allenes; Academic Press: New York, 1982. (d) Lu, X.; Zhang, C.; Xu, Z. Acc. Chem. Res. 2001, 34, 535.
37. For a review on transition metal-catalyzed reactions of allenes, see: (e) Hashmi, A. S. K. Angew. Chem., Int. Ed. 2001, 39, 3590.
38. For a review on palladium-allene chemistry, see: (f) Zimmer, R.; Dinesh, C. U.; Nandanan, E.; Khan, F. A. Chem. Rev. 2000, 100, 3067.
39. For a review on transition metal-based cyclization of allenes, see: (g) Bates, R. W.; Satcharoen, V. Chem. Soc. Rev. 2002, 31, 12.
40. For a selected recent paper on the asymmetric synthesis of oxygenated heterocycles from allenes, see: (h) Xu, D.; Li, Z.; Ma, S. Chem. Eur. J. 2002, 8, 5012.
41. See, for instance: (a) Alcaide, B.; Almendros, P.; Aragoncillo, C. Chem. Eur. J. 2002, 8, 1719. (b) Alcaide, B.; Almendros, P.; Aragoncillo, C.; Redondo, M. C. Chem. Commun. 2002, 1472. (c) Alcaide, B.; Almendros, P.; Aragoncillo, C. Chem. Eur. J. 2002, 8, 3646. (d) Alcaide, B.; Almendros, P.; Alonso, J. M.; Aly, M. F.; Pardo, C.; Sáez, E.; Torres, M. R. J. Org. Chem. 2002, 67, 7004. (e) Alcaide, B.; Almendros, P.; Alonso, J. M.; Redondo, M. C. J. Org. Chem. 2003, 68, 1426.
42. See, for instance: (a) Alcaide, B.; Almendros, P.; Aragoncillo, C. Chem. Eur. J. 2002, 8, 1719. (b) Alcaide, B.; Almendros, P.; Aragoncillo, C.; Redondo, M. C. Chem. Commun. 2002, 1472. (c) Alcaide, B.; Almendros, P.; Aragoncillo, C. Chem. Eur. J. 2002, 8, 3646. (d) Alcaide, B.; Almendros, P.; Alonso, J. M.; Aly, M. F.; Pardo, C.; Sáez, E.; Torres, M. R. J. Org. Chem. 2002, 67, 7004. (e) Alcaide, B.; Almendros, P.; Alonso, J. M.; Redondo, M. C. J. Org. Chem. 2003, 68, 1426.
43. See, for instance: (a) Alcaide, B.; Almendros, P.; Aragoncillo, C. Chem. Eur. J. 2002, 8, 1719. (b) Alcaide, B.; Almendros, P.; Aragoncillo, C.; Redondo, M. C. Chem. Commun. 2002, 1472. (c) Alcaide, B.; Almendros, P.; Aragoncillo, C. Chem. Eur. J. 2002, 8, 3646. (d) Alcaide, B.; Almendros, P.; Alonso, J. M.; Aly, M. F.; Pardo, C.; Sáez, E.; Torres, M. R. J. Org. Chem. 2002, 67, 7004. (e) Alcaide, B.; Almendros, P.; Alonso, J. M.; Redondo, M. C. J. Org. Chem. 2003, 68, 1426.
44. See, for instance: (a) Alcaide, B.; Almendros, P.; Aragoncillo, C. Chem. Eur. J. 2002, 8, 1719. (b) Alcaide, B.; Almendros, P.; Aragoncillo, C.; Redondo, M. C. Chem. Commun. 2002, 1472. (c) Alcaide, B.; Almendros, P.; Aragoncillo, C. Chem. Eur. J. 2002, 8, 3646. (d) Alcaide, B.; Almendros, P.; Alonso, J. M.; Aly, M. F.; Pardo, C.; Sáez, E.; Torres, M. R. J. Org. Chem. 2002, 67, 7004. (e) Alcaide, B.; Almendros, P.; Alonso, J. M.; Redondo, M. C. J. Org. Chem. 2003, 68, 1426.
45. See, for instance: (a) Alcaide, B.; Almendros, P.; Aragoncillo, C. Chem. Eur. J. 2002, 8, 1719. (b) Alcaide, B.; Almendros, P.; Aragoncillo, C.; Redondo, M. C. Chem. Commun. 2002, 1472. (c) Alcaide, B.; Almendros, P.; Aragoncillo, C. Chem. Eur. J. 2002, 8, 3646. (d) Alcaide, B.; Almendros, P.; Alonso, J. M.; Aly, M. F.; Pardo, C.; Sáez, E.; Torres, M. R. J. Org. Chem. 2002, 67, 7004. (e) Alcaide, B.; Almendros, P.; Alonso, J. M.; Redondo, M. C. J. Org. Chem. 2003, 68, 1426.
46. (a) Alcaide, B.; Martín-Cantalejo, Y.; Plumet, J.; Rodríguez-López, J.; Sierra, M. A. Tetrahedron Lett. 1991, 32, 803.
47. (b) Alcaide, B.; Martín-Cantalejo, Y.; Pérez-Castells, J.; Rodríguez-López, J.; Sierra, M. A.; Monge, A.; Pérez-García, V. J. Org. Chem. 1992, 57, 5921.
48. Elliot, R. L.; Nicholson, N. H.; Peaker, F. E.; Takle, A. K.; Richardson, C. M.; Tyler, J. W.; White, J.; Pearson, M. J.; Eggleston, D. S.; Haltiwanger, R. C. J. Org. Chem. 1997, 62, 4998
49. Allene moiety was originally thought to be very unstable (prior to the 1970s, allenes were regarded as curiosities) and, in fact, upon undergoing any addition reaction, experiences a relief in strain of about 10 kcal/mol: Padwa, A.; Filipkowski, M. A.; Meske, M.; Murphree, S. S.; Watterson, S. H.; Ni, Z. J. Org. Chem. 1994, 59, 591.
50. Methodology of the asymmetric formation of cyclobutane derivatives is limited in preparative organic chemistry. For example, see: Methods of Organic Chemistry (Houben-Weyl); De Meijere, A., Ed.; Thieme: Stuttgart, 1997; Vol. E17e.
51. (a) Skattebøl, L.; Stenstrøm, Y. Tetrahedron Lett. 1983, 24, 3021.
52. (b) Nair, V.; Sethumadhavan, D.; Nair, S. M.; Shanmugam, P.; Treesa, P. M.; Eigendorf, G. K. Synlett 2002, 1655.
53. (c) Hansen, T. V.; Skattebøl, L.; Stenstrøm, Y. Tetrahedron 2003, 59, 3461.
54. Padwa, A.; Meske, M.; Murphree, S.; Watterson, S. H.; Ni, Z. J. Am. Chem. Soc. 1995, 117, 7071.
55. For leading references, see: (a) Radicals in Organic Synthesis, Renaud, P., Sibi, M. P., Eds.; Wiley-VCH: Weinheim, Germany, 2002. (b) Curran, D. P.; Porter, N. A.; Giese, B. In Stereochemistry of Radical Reactions; VCH Publishers: New York, 1996. (c) Giese, B.; Kopping, B.; Göbel, T.; Dickhaut, J.; Thoma, G.; Kulicke, K. J.; Trach, F. Org. React. 1996, 48, 301-856. (d) Fossey, J.; Lefort, D.; Sorba, J. Free Radicals in Organic Chemistry; John Wiley & Sons: New York, 1995. (e) Barton, D. H. R.; Parekh, S. I. Half a Century of Free Radical Chemistry; Cambridge University Press: Cambridge, 1993. (f) Motherwell, W. B.; Crich, D. Free Radical Chain Reactions in Organic Synthesis; Academic Press: London, 1992. (g) Curran, D. P. In Comprehesive Organic Synthesis; Trost, B. M., Ed.; Pergamon: Oxford, 1992; Vol 4, Chapter 4.2. (h) Jasperse, C. P.; Curran, D. P.; Fevig, T. L. Chem. Rev. 1991, 91, 1237. (i) Curran, D. P. Synthesis 1988, 417. (j) Curran, D. P. Synthesis 1988, 489.
56. For leading references, see: (a) Radicals in Organic Synthesis, Renaud, P., Sibi, M. P., Eds.; Wiley-VCH: Weinheim, Germany, 2002. (b) Curran, D. P.; Porter, N. A.; Giese, B. In Stereochemistry of Radical Reactions; VCH Publishers: New York, 1996. (c) Giese, B.; Kopping, B.; Göbel, T.; Dickhaut, J.; Thoma, G.; Kulicke, K. J.; Trach, F. Org. React. 1996, 48, 301-856. (d) Fossey, J.; Lefort, D.; Sorba, J. Free Radicals in Organic Chemistry; John Wiley & Sons: New York, 1995. (e) Barton, D. H. R.; Parekh, S. I. Half a Century of Free Radical Chemistry; Cambridge University Press: Cambridge, 1993. (f) Motherwell, W. B.; Crich, D. Free Radical Chain Reactions in Organic Synthesis; Academic Press: London, 1992. (g) Curran, D. P. In Comprehesive Organic Synthesis; Trost, B. M., Ed.; Pergamon: Oxford, 1992; Vol 4, Chapter 4.2. (h) Jasperse, C. P.; Curran, D. P.; Fevig, T. L. Chem. Rev. 1991, 91, 1237. (i) Curran, D. P. Synthesis 1988, 417. (j) Curran, D. P. Synthesis 1988, 489.
57. For leading references, see: (a) Radicals in Organic Synthesis, Renaud, P., Sibi, M. P., Eds.; Wiley-VCH: Weinheim, Germany, 2002. (b) Curran, D. P.; Porter, N. A.; Giese, B. In Stereochemistry of Radical Reactions; VCH Publishers: New York, 1996. (c) Giese, B.; Kopping, B.; Göbel, T.; Dickhaut, J.; Thoma, G.; Kulicke, K. J.; Trach, F. Org. React. 1996, 48, 301-856. (d) Fossey, J.; Lefort, D.; Sorba, J. Free Radicals in Organic Chemistry; John Wiley & Sons: New York, 1995. (e) Barton, D. H. R.; Parekh, S. I. Half a Century of Free Radical Chemistry; Cambridge University Press: Cambridge, 1993. (f) Motherwell, W. B.; Crich, D. Free Radical Chain Reactions in Organic Synthesis; Academic Press: London, 1992. (g) Curran, D. P. In Comprehesive Organic Synthesis; Trost, B. M., Ed.; Pergamon: Oxford, 1992; Vol 4, Chapter 4.2. (h) Jasperse, C. P.; Curran, D. P.; Fevig, T. L. Chem. Rev. 1991, 91, 1237. (i) Curran, D. P. Synthesis 1988, 417. (j) Curran, D. P. Synthesis 1988, 489.
58. For leading references, see: (a) Radicals in Organic Synthesis, Renaud, P., Sibi, M. P., Eds.; Wiley-VCH: Weinheim, Germany, 2002. (b) Curran, D. P.; Porter, N. A.; Giese, B. In Stereochemistry of Radical Reactions; VCH Publishers: New York, 1996. (c) Giese, B.; Kopping, B.; Göbel, T.; Dickhaut, J.; Thoma, G.; Kulicke, K. J.; Trach, F. Org. React. 1996, 48, 301-856. (d) Fossey, J.; Lefort, D.; Sorba, J. Free Radicals in Organic Chemistry; John Wiley & Sons: New York, 1995. (e) Barton, D. H. R.; Parekh, S. I. Half a Century of Free Radical Chemistry; Cambridge University Press: Cambridge, 1993. (f) Motherwell, W. B.; Crich, D. Free Radical Chain Reactions in Organic Synthesis; Academic Press: London, 1992. (g) Curran, D. P. In Comprehesive Organic Synthesis; Trost, B. M., Ed.; Pergamon: Oxford, 1992; Vol 4, Chapter 4.2. (h) Jasperse, C. P.; Curran, D. P.; Fevig, T. L. Chem. Rev. 1991, 91, 1237. (i) Curran, D. P. Synthesis 1988, 417. (j) Curran, D. P. Synthesis 1988, 489.
59. For leading references, see: (a) Radicals in Organic Synthesis, Renaud, P., Sibi, M. P., Eds.; Wiley-VCH: Weinheim, Germany, 2002. (b) Curran, D. P.; Porter, N. A.; Giese, B. In Stereochemistry of Radical Reactions; VCH Publishers: New York, 1996. (c) Giese, B.; Kopping, B.; Göbel, T.; Dickhaut, J.; Thoma, G.; Kulicke, K. J.; Trach, F. Org. React. 1996, 48, 301-856. (d) Fossey, J.; Lefort, D.; Sorba, J. Free Radicals in Organic Chemistry; John Wiley & Sons: New York, 1995. (e) Barton, D. H. R.; Parekh, S. I. Half a Century of Free Radical Chemistry; Cambridge University Press: Cambridge, 1993. (f) Motherwell, W. B.; Crich, D. Free Radical Chain Reactions in Organic Synthesis; Academic Press: London, 1992. (g) Curran, D. P. In Comprehesive Organic Synthesis; Trost, B. M., Ed.; Pergamon: Oxford, 1992; Vol 4, Chapter 4.2. (h) Jasperse, C. P.; Curran, D. P.; Fevig, T. L. Chem. Rev. 1991, 91, 1237. (i) Curran, D. P. Synthesis 1988, 417. (j) Curran, D. P. Synthesis 1988, 489.
60. For leading references, see: (a) Radicals in Organic Synthesis, Renaud, P., Sibi, M. P., Eds.; Wiley-VCH: Weinheim, Germany, 2002. (b) Curran, D. P.; Porter, N. A.; Giese, B. In Stereochemistry of Radical Reactions; VCH Publishers: New York, 1996. (c) Giese, B.; Kopping, B.; Göbel, T.; Dickhaut, J.; Thoma, G.; Kulicke, K. J.; Trach, F. Org. React. 1996, 48, 301-856. (d) Fossey, J.; Lefort, D.; Sorba, J. Free Radicals in Organic Chemistry; John Wiley & Sons: New York, 1995. (e) Barton, D. H. R.; Parekh, S. I. Half a Century of Free Radical Chemistry; Cambridge University Press: Cambridge, 1993. (f) Motherwell, W. B.; Crich, D. Free Radical Chain Reactions in Organic Synthesis; Academic Press: London, 1992. (g) Curran, D. P. In Comprehesive Organic Synthesis; Trost, B. M., Ed.; Pergamon: Oxford, 1992; Vol 4, Chapter 4.2. (h) Jasperse, C. P.; Curran, D. P.; Fevig, T. L. Chem. Rev. 1991, 91, 1237. (i) Curran, D. P. Synthesis 1988, 417. (j) Curran, D. P. Synthesis 1988, 489.
61. For leading references, see: (a) Radicals in Organic Synthesis, Renaud, P., Sibi, M. P., Eds.; Wiley-VCH: Weinheim, Germany, 2002. (b) Curran, D. P.; Porter, N. A.; Giese, B. In Stereochemistry of Radical Reactions; VCH Publishers: New York, 1996. (c) Giese, B.; Kopping, B.; Göbel, T.; Dickhaut, J.; Thoma, G.; Kulicke, K. J.; Trach, F. Org. React. 1996, 48, 301-856. (d) Fossey, J.; Lefort, D.; Sorba, J. Free Radicals in Organic Chemistry; John Wiley & Sons: New York, 1995. (e) Barton, D. H. R.; Parekh, S. I. Half a Century of Free Radical Chemistry; Cambridge University Press: Cambridge, 1993. (f) Motherwell, W. B.; Crich, D. Free Radical Chain Reactions in Organic Synthesis; Academic Press: London, 1992. (g) Curran, D. P. In Comprehesive Organic Synthesis; Trost, B. M., Ed.; Pergamon: Oxford, 1992; Vol 4, Chapter 4.2. (h) Jasperse, C. P.; Curran, D. P.; Fevig, T. L. Chem. Rev. 1991, 91, 1237. (i) Curran, D. P. Synthesis 1988, 417. (j) Curran, D. P. Synthesis 1988, 489.
62. For leading references, see: (a) Radicals in Organic Synthesis, Renaud, P., Sibi, M. P., Eds.; Wiley-VCH: Weinheim, Germany, 2002. (b) Curran, D. P.; Porter, N. A.; Giese, B. In Stereochemistry of Radical Reactions; VCH Publishers: New York, 1996. (c) Giese, B.; Kopping, B.; Göbel, T.; Dickhaut, J.; Thoma, G.; Kulicke, K. J.; Trach, F. Org. React. 1996, 48, 301-856. (d) Fossey, J.; Lefort, D.; Sorba, J. Free Radicals in Organic Chemistry; John Wiley & Sons: New York, 1995. (e) Barton, D. H. R.; Parekh, S. I. Half a Century of Free Radical Chemistry; Cambridge University Press: Cambridge, 1993. (f) Motherwell, W. B.; Crich, D. Free Radical Chain Reactions in Organic Synthesis; Academic Press: London, 1992. (g) Curran, D. P. In Comprehesive Organic Synthesis; Trost, B. M., Ed.; Pergamon: Oxford, 1992; Vol 4, Chapter 4.2. (h) Jasperse, C. P.; Curran, D. P.; Fevig, T. L. Chem. Rev. 1991, 91, 1237. (i) Curran, D. P. Synthesis 1988, 417. (j) Curran, D. P. Synthesis 1988, 489.
63. For leading references, see: (a) Radicals in Organic Synthesis, Renaud, P., Sibi, M. P., Eds.; Wiley-VCH: Weinheim, Germany, 2002. (b) Curran, D. P.; Porter, N. A.; Giese, B. In Stereochemistry of Radical Reactions; VCH Publishers: New York, 1996. (c) Giese, B.; Kopping, B.; Göbel, T.; Dickhaut, J.; Thoma, G.; Kulicke, K. J.; Trach, F. Org. React. 1996, 48, 301-856. (d) Fossey, J.; Lefort, D.; Sorba, J. Free Radicals in Organic Chemistry; John Wiley & Sons: New York, 1995. (e) Barton, D. H. R.; Parekh, S. I. Half a Century of Free Radical Chemistry; Cambridge University Press: Cambridge, 1993. (f) Motherwell, W. B.; Crich, D. Free Radical Chain Reactions in Organic Synthesis; Academic Press: London, 1992. (g) Curran, D. P. In Comprehesive Organic Synthesis; Trost, B. M., Ed.; Pergamon: Oxford, 1992; Vol 4, Chapter 4.2. (h) Jasperse, C. P.; Curran, D. P.; Fevig, T. L. Chem. Rev. 1991, 91, 1237. (i) Curran, D. P. Synthesis 1988, 417. (j) Curran, D. P. Synthesis 1988, 489.
64. For leading references, see: (a) Radicals in Organic Synthesis, Renaud, P., Sibi, M. P., Eds.; Wiley-VCH: Weinheim, Germany, 2002. (b) Curran, D. P.; Porter, N. A.; Giese, B. In Stereochemistry of Radical Reactions; VCH Publishers: New York, 1996. (c) Giese, B.; Kopping, B.; Göbel, T.; Dickhaut, J.; Thoma, G.; Kulicke, K. J.; Trach, F. Org. React. 1996, 48, 301-856. (d) Fossey, J.; Lefort, D.; Sorba, J. Free Radicals in Organic Chemistry; John Wiley & Sons: New York, 1995. (e) Barton, D. H. R.; Parekh, S. I. Half a Century of Free Radical Chemistry; Cambridge University Press: Cambridge, 1993. (f) Motherwell, W. B.; Crich, D. Free Radical Chain Reactions in Organic Synthesis; Academic Press: London, 1992. (g) Curran, D. P. In Comprehesive Organic Synthesis; Trost, B. M., Ed.; Pergamon: Oxford, 1992; Vol 4, Chapter 4.2. (h) Jasperse, C. P.; Curran, D. P.; Fevig, T. L. Chem. Rev. 1991, 91, 1237. (i) Curran, D. P. Synthesis 1988, 417. (j) Curran, D. P. Synthesis 1988, 489.
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67. (c) Truce, W. E.; Heuring, D. L.; Wolf, G. C. J. Org. Chem. 1974, 39, 238.
68. Although construction of medium-sized rings using free radical methodology is difficult to achieve, we and others were able to prepare medium-sized rings fused to 2-azetidinones. See: (a) Alcaide, B.; Almendros, P. ; Pardo, C.; Rodríguez-Ranera, C.; Rodríguez-Vicente, V. J. Org. Chem. 2003, 68, 3106. (b) Alcaide, B.; Almendros, P.; Aragoncillo, C. J. Org. Chem. 2001, 66, 1612. (c) Penfold, D. J.; Pike, K.; Genge, A.; Anson, M.; Kitteringham, J.; Kilburn, J. D. Tetrahedron Lett. 2000, 41, 10347. (d) Knight, J.; Parsons, P. J. J. Chem. Soc., Perkin Trans. 1 1987, 1237. (e) Knight, J.; Parsons, P. J.; Southgate, R. J. Chem. Soc., Chem. Commun. 1986, 78.
69. Although construction of medium-sized rings using free radical methodology is difficult to achieve, we and others were able to prepare medium-sized rings fused to 2-azetidinones. See: (a) Alcaide, B.; Almendros, P. ; Pardo, C.; Rodríguez-Ranera, C.; Rodríguez-Vicente, V. J. Org. Chem. 2003, 68, 3106. (b) Alcaide, B.; Almendros, P.; Aragoncillo, C. J. Org. Chem. 2001, 66, 1612. (c) Penfold, D. J.; Pike, K.; Genge, A.; Anson, M.; Kitteringham, J.; Kilburn, J. D. Tetrahedron Lett. 2000, 41, 10347. (d) Knight, J.; Parsons, P. J. J. Chem. Soc., Perkin Trans. 1 1987, 1237. (e) Knight, J.; Parsons, P. J.; Southgate, R. J. Chem. Soc., Chem. Commun. 1986, 78.
70. Although construction of medium-sized rings using free radical methodology is difficult to achieve, we and others were able to prepare medium-sized rings fused to 2-azetidinones. See: (a) Alcaide, B.; Almendros, P. ; Pardo, C.; Rodríguez-Ranera, C.; Rodríguez-Vicente, V. J. Org. Chem. 2003, 68, 3106. (b) Alcaide, B.; Almendros, P.; Aragoncillo, C. J. Org. Chem. 2001, 66, 1612. (c) Penfold, D. J.; Pike, K.; Genge, A.; Anson, M.; Kitteringham, J.; Kilburn, J. D. Tetrahedron Lett. 2000, 41, 10347. (d) Knight, J.; Parsons, P. J. J. Chem. Soc., Perkin Trans. 1 1987, 1237. (e) Knight, J.; Parsons, P. J.; Southgate, R. J. Chem. Soc., Chem. Commun. 1986, 78.
71. Although construction of medium-sized rings using free radical methodology is difficult to achieve, we and others were able to prepare medium-sized rings fused to 2-azetidinones. See: (a) Alcaide, B.; Almendros, P. ; Pardo, C.; Rodríguez-Ranera, C.; Rodríguez-Vicente, V. J. Org. Chem. 2003, 68, 3106. (b) Alcaide, B.; Almendros, P.; Aragoncillo, C. J. Org. Chem. 2001, 66, 1612. (c) Penfold, D. J.; Pike, K.; Genge, A.; Anson, M.; Kitteringham, J.; Kilburn, J. D. Tetrahedron Lett. 2000, 41, 10347. (d) Knight, J.; Parsons, P. J. J. Chem. Soc., Perkin Trans. 1 1987, 1237. (e) Knight, J.; Parsons, P. J.; Southgate, R. J. Chem. Soc., Chem. Commun. 1986, 78.
72. Although construction of medium-sized rings using free radical methodology is difficult to achieve, we and others were able to prepare medium-sized rings fused to 2-azetidinones. See: (a) Alcaide, B.; Almendros, P. ; Pardo, C.; Rodríguez-Ranera, C.; Rodríguez-Vicente, V. J. Org. Chem. 2003, 68, 3106. (b) Alcaide, B.; Almendros, P.; Aragoncillo, C. J. Org. Chem. 2001, 66, 1612. (c) Penfold, D. J.; Pike, K.; Genge, A.; Anson, M.; Kitteringham, J.; Kilburn, J. D. Tetrahedron Lett. 2000, 41, 10347. (d) Knight, J.; Parsons, P. J. J. Chem. Soc., Perkin Trans. 1 1987, 1237. (e) Knight, J.; Parsons, P. J.; Southgate, R. J. Chem. Soc., Chem. Commun. 1986, 78.