Tandem functionalization of nonactivated alkenes and alkynes in intramolecular N-acyloxyiminium ion carbocyclization. Synthesis of 6-substituted hydroindole 2-carboxylic acids

Organic Letters

Volumn 6, Issue 25, 2004, Pages 4683-4686

  Hanessian, Stephen ^a   Tremblay, Martin ^a  

^a UNIVERSITÉ DE MONTRÉAL   (Canada)

Author keywords

[No Author keywords available]

Indexed keywords

2 INDOLECARBOXYLIC ACID; ALKENE DERIVATIVE; ALKYNE DERIVATIVE; BROMINE DERIVATIVE; CARBOXYLIC ACID DERIVATIVE; IMINE; INDOLE DERIVATIVE; LEWIS ACID; PALLADIUM; UNCLASSIFIED DRUG; VINYL BROMIDE;

ARTICLE; ARYLATION; CATALYSIS; CATALYST; CHEMICAL REACTION; CYCLIZATION; ENANTIOMER; FRIEDEL CRAFTS REACTION; HECK REACTION; MIYAURA COUPLING REACTION; STEREOCHEMISTRY; STILLE REACTION; SUBSTITUTION REACTION; SUZUKI REACTION; SYNTHESIS;

EID: 11444254435     PISSN: 15237060     EISSN: None     Source Type: Journal    
DOI: 10.1021/ol040053b     Document Type: Article

References (83)

1. (a) Rios Steiner, J. L.; Murakami, M.; Tulinsky, A. J. Am. Chem. Soc. 1998, 120, 597.
2. (b) Matsuda, H.; Okino, T.; Murakami, M.; Yamaguchi, K. Tetrahedron 1996, 52, 14501.
3. (c) Murakami, M.; Ishida, K.; Okino, T.; Okita, Y.; Matsuda, H.; Yamaguchi, K. Tetrahedron Lett. 1995, 36, 2785.
4. (d) Murakami, M.; Okita, Y.; Matsuda, H.; Okino, H.; Yamaguchi, K.; Tetrahedron Lett. 1994, 35, 3129.
5. Carroll, A. R.; Pierens, G.; Fechner, G.; de Almeidaleona, P.; Ngo, A.; Simpson, M.; Hooper, J. N. A.; Böstrom, S. L.; Musil, D.; Quinn, R. J. J. Am. Chem. Soc. 2002, 124, 13340.
6. (a) Vincent, M.; Marchand, B.; Remond, G.; Jaguelin-Guinamant, S.; Damien, G.; Portevin, B.; Baumal, J. Y.; Volland, J. P. Drug Design and Discovery 1992, 9, 11.
7. For related structures (ramipril), see: (b) Warner, G. T.; Perry, C. M. Drugs 2002, 62, 1381.
8. For recent reviews, see: (a) Leusch, H.; Harrigan, G. G.; Goetz, G.; Horgen, F. D. Curr. Med. Chem. 2002, 9, 179. (b) Burja, A. M.; Banaigs, B.; Abou-Mansour, E.; Burgess, J.-G.; Wright, P. C. Tetrahedron 2001, 57, 9347. (c) Shiori, T.; Hamada, Y. Synlett 2001, 184. (d) Lewis, J. R. Nat. Prod. Rep. 1998, 417. (e) Namikoshi, M.; Rinehart, K. L. J. Indust. Microbiol. 1996, 17, 373. (f) Rinehart, K. L.; Namikoshi, M.; Choi, B. W. J. Appl. Phycol. 1994, 6, 159.
9. For recent reviews, see: (a) Leusch, H.; Harrigan, G. G.; Goetz, G.; Horgen, F. D. Curr. Med. Chem. 2002, 9, 179. (b) Burja, A. M.; Banaigs, B.; Abou-Mansour, E.; Burgess, J.-G.; Wright, P. C. Tetrahedron 2001, 57, 9347. (c) Shiori, T.; Hamada, Y. Synlett 2001, 184. (d) Lewis, J. R. Nat. Prod. Rep. 1998, 417. (e) Namikoshi, M.; Rinehart, K. L. J. Indust. Microbiol. 1996, 17, 373. (f) Rinehart, K. L.; Namikoshi, M.; Choi, B. W. J. Appl. Phycol. 1994, 6, 159.
10. For recent reviews, see: (a) Leusch, H.; Harrigan, G. G.; Goetz, G.; Horgen, F. D. Curr. Med. Chem. 2002, 9, 179. (b) Burja, A. M.; Banaigs, B.; Abou-Mansour, E.; Burgess, J.-G.; Wright, P. C. Tetrahedron 2001, 57, 9347. (c) Shiori, T.; Hamada, Y. Synlett 2001, 184. (d) Lewis, J. R. Nat. Prod. Rep. 1998, 417. (e) Namikoshi, M.; Rinehart, K. L. J. Indust. Microbiol. 1996, 17, 373. (f) Rinehart, K. L.; Namikoshi, M.; Choi, B. W. J. Appl. Phycol. 1994, 6, 159.
11. For recent reviews, see: (a) Leusch, H.; Harrigan, G. G.; Goetz, G.; Horgen, F. D. Curr. Med. Chem. 2002, 9, 179. (b) Burja, A. M.; Banaigs, B.; Abou-Mansour, E.; Burgess, J.-G.; Wright, P. C. Tetrahedron 2001, 57, 9347. (c) Shiori, T.; Hamada, Y. Synlett 2001, 184. (d) Lewis, J. R. Nat. Prod. Rep. 1998, 417. (e) Namikoshi, M.; Rinehart, K. L. J. Indust. Microbiol. 1996, 17, 373. (f) Rinehart, K. L.; Namikoshi, M.; Choi, B. W. J. Appl. Phycol. 1994, 6, 159.
12. For recent reviews, see: (a) Leusch, H.; Harrigan, G. G.; Goetz, G.; Horgen, F. D. Curr. Med. Chem. 2002, 9, 179. (b) Burja, A. M.; Banaigs, B.; Abou-Mansour, E.; Burgess, J.-G.; Wright, P. C. Tetrahedron 2001, 57, 9347. (c) Shiori, T.; Hamada, Y. Synlett 2001, 184. (d) Lewis, J. R. Nat. Prod. Rep. 1998, 417. (e) Namikoshi, M.; Rinehart, K. L. J. Indust. Microbiol. 1996, 17, 373. (f) Rinehart, K. L.; Namikoshi, M.; Choi, B. W. J. Appl. Phycol. 1994, 6, 159.
13. For recent reviews, see: (a) Leusch, H.; Harrigan, G. G.; Goetz, G.; Horgen, F. D. Curr. Med. Chem. 2002, 9, 179. (b) Burja, A. M.; Banaigs, B.; Abou-Mansour, E.; Burgess, J.-G.; Wright, P. C. Tetrahedron 2001, 57, 9347. (c) Shiori, T.; Hamada, Y. Synlett 2001, 184. (d) Lewis, J. R. Nat. Prod. Rep. 1998, 417. (e) Namikoshi, M.; Rinehart, K. L. J. Indust. Microbiol. 1996, 17, 373. (f) Rinehart, K. L.; Namikoshi, M.; Choi, B. W. J. Appl. Phycol. 1994, 6, 159.
14. (a) Wipf, P.; Methot, J.-L. Org. Lett. 2000, 2, 4213.
15. (b) Wipf, P.; Maresko, D. A. Tetrahedron Lett. 2000, 41, 4723.
16. (c) Wipf, P.; Li, W. J. Org. Chem. 1999, 64, 4576.
17. (d) Wipf, P.; Kim, Y.; Goustein, D. M. J. Am. Chem. Soc. 1995, 177, 1106.
18. (a) Valls, N.; López-Canet, M.; Vallribera, M.; Bonjoch, J. Chem. Eur. J. 2001, 7, 3446.
19. (b) Valls, N.; López-Canet, M.; Vallribera, M.; Bonjoch, J. J. Am. Chem. Soc. 2000, 122, 11248.
20. (c) Bonjoch, J.; Catena, J.; Isabal, E.; López-Canet, M.; Valls, N. Tetrahedron: Asymmetry 1996, 7. 1899.
21. (d) Bonjoch, J.; Catena, J.; Valls, N. J. Org. Chem. 1996, 61, 7106.
22. Ohshima, T.; Gnanadesikan, V.; Shibughushi, T.; Fukuta, Y.; Nemoto, T.; Shibasaki, M. J. Am. Chem. Soc. 2003, 125, 11206.
23. Hanessian, S.; Margarita, R.; Hall, A.; Johnstone, S.; Tremblay, M.; Parlanti, L. J. Am. Chem. Soc. 2002, 124, 13342.
24. Belvisi, L.; Colombo, L.; DiGiacomo, M.; Manzoni, L.; Vodopivec, B.; Scolastico, C. Tetrahedron 2001, 57, 6463.
25. Toyooka, N.; Okumura, M.; Himiyama, T.; Nakazawa, A.; Nemoto, H. Synlett 2003, 55.
26. Hanessian, S.; Tremblay, M.; Petersen, J. W. J. Am. Chem. Soc. 2004, 126, 6064.
27. Mayr, H.; Kempf, B.; Ofial, A. R. Acc. Chem. Res. 2003, 36, 66.
28. For selected examples of intermolecular Friedel - Crafts-type C-arylation of N-acyloxyiminium ions, see: (a) Manfré, F.; Pulicani, J. P. Tetrahedron: Asymmetry 1994, 5, 235. (b) Matsumura, Y.; Terauchi, J.; Yamamoto, T.; Konno, T.; Shono, T. Tetrahedron 1993, 49, 8503. (c) Malmberg, M.; Nyberg, K. Acta Chem. Scand. 1981, B35, 411. See also ref 18.
29. For selected examples of intermolecular Friedel - Crafts-type C-arylation of N-acyloxyiminium ions, see: (a) Manfré, F.; Pulicani, J. P. Tetrahedron: Asymmetry 1994, 5, 235. (b) Matsumura, Y.; Terauchi, J.; Yamamoto, T.; Konno, T.; Shono, T. Tetrahedron 1993, 49, 8503. (c) Malmberg, M.; Nyberg, K. Acta Chem. Scand. 1981, B35, 411. See also ref 18.
30. For selected examples of intermolecular Friedel - Crafts-type C-arylation of N-acyloxyiminium ions, see: (a) Manfré, F.; Pulicani, J. P. Tetrahedron: Asymmetry 1994, 5, 235. (b) Matsumura, Y.; Terauchi, J.; Yamamoto, T.; Konno, T.; Shono, T. Tetrahedron 1993, 49, 8503. (c) Malmberg, M.; Nyberg, K. Acta Chem. Scand. 1981, B35, 411. See also ref 18.
31. For examples, see: (a) Ent, H.; de Koning, H.; Speckamp, W. N. J. Org. Chem. 1986, 51, 1687. (b) Schoemaker, H. E.; Speckamp, W. N. Tetrahedron Lett. 1978, 1515. (c) Hart, D. J.; Kanai, K. J. Am. Chem. Soc. 1983, 103, 1255. For Prins cyclization, see: (d) Jaber, J. J.; Mitsui, K.; Rychnovsky, S. D. J. Org. Chem. 2001, 66, 4079. For related examples of stereoelectronic effects in the intermolecular addition of nucleophiles to iminium ions, see: (e) Heathcock, C. H.; Kleinman, E. F.; Binkley, E. S. J. Am. Chem. Soc. 1982, 104, 1054. (f) Demailly, G.; Solladié, G. J. Org. Chem. 1981, 46, 3102. (g) Overman, L. E.; Freerks, R. L. J. Org. Chem. 1981, 46, 6, 2833. (h) Overman, L. E.; Fukaya, C. J. Am. Chem. Soc. 1980, 102, 1454. (i) Stevens, R. V.; Lee, A. W. M. J. Am. Chem. Soc. 1979, 101, 7032. (j) Wenkert, E.; Chang, C.-J.; Chawla, H. P. S.; Cochran, D. W.; Hagaman, E. W.; King, J. C.; Orito, K. J. Am. Chem. Soc. 1976, 98, 3645. (k) Ziegler, F. E.; Spitzner, E. B. J. Am. Chem. Soc. 1973, 95, 7146. (l) Deslongchamps, P. Stereoelectronic Effects in Organic Chemistry, Pergamon: New York, 1983; Chapter 6.
32. For examples, see: (a) Ent, H.; de Koning, H.; Speckamp, W. N. J. Org. Chem. 1986, 51, 1687. (b) Schoemaker, H. E.; Speckamp, W. N. Tetrahedron Lett. 1978, 1515. (c) Hart, D. J.; Kanai, K. J. Am. Chem. Soc. 1983, 103, 1255. For Prins cyclization, see: (d) Jaber, J. J.; Mitsui, K.; Rychnovsky, S. D. J. Org. Chem. 2001, 66, 4079. For related examples of stereoelectronic effects in the intermolecular addition of nucleophiles to iminium ions, see: (e) Heathcock, C. H.; Kleinman, E. F.; Binkley, E. S. J. Am. Chem. Soc. 1982, 104, 1054. (f) Demailly, G.; Solladié, G. J. Org. Chem. 1981, 46, 3102. (g) Overman, L. E.; Freerks, R. L. J. Org. Chem. 1981, 46, 6, 2833. (h) Overman, L. E.; Fukaya, C. J. Am. Chem. Soc. 1980, 102, 1454. (i) Stevens, R. V.; Lee, A. W. M. J. Am. Chem. Soc. 1979, 101, 7032. (j) Wenkert, E.; Chang, C.-J.; Chawla, H. P. S.; Cochran, D. W.; Hagaman, E. W.; King, J. C.; Orito, K. J. Am. Chem. Soc. 1976, 98, 3645. (k) Ziegler, F. E.; Spitzner, E. B. J. Am. Chem. Soc. 1973, 95, 7146. (l) Deslongchamps, P. Stereoelectronic Effects in Organic Chemistry, Pergamon: New York, 1983; Chapter 6.
33. For examples, see: (a) Ent, H.; de Koning, H.; Speckamp, W. N. J. Org. Chem. 1986, 51, 1687. (b) Schoemaker, H. E.; Speckamp, W. N. Tetrahedron Lett. 1978, 1515. (c) Hart, D. J.; Kanai, K. J. Am. Chem. Soc. 1983, 103, 1255. For Prins cyclization, see: (d) Jaber, J. J.; Mitsui, K.; Rychnovsky, S. D. J. Org. Chem. 2001, 66, 4079. For related examples of stereoelectronic effects in the intermolecular addition of nucleophiles to iminium ions, see: (e) Heathcock, C. H.; Kleinman, E. F.; Binkley, E. S. J. Am. Chem. Soc. 1982, 104, 1054. (f) Demailly, G.; Solladié, G. J. Org. Chem. 1981, 46, 3102. (g) Overman, L. E.; Freerks, R. L. J. Org. Chem. 1981, 46, 6, 2833. (h) Overman, L. E.; Fukaya, C. J. Am. Chem. Soc. 1980, 102, 1454. (i) Stevens, R. V.; Lee, A. W. M. J. Am. Chem. Soc. 1979, 101, 7032. (j) Wenkert, E.; Chang, C.-J.; Chawla, H. P. S.; Cochran, D. W.; Hagaman, E. W.; King, J. C.; Orito, K. J. Am. Chem. Soc. 1976, 98, 3645. (k) Ziegler, F. E.; Spitzner, E. B. J. Am. Chem. Soc. 1973, 95, 7146. (l) Deslongchamps, P. Stereoelectronic Effects in Organic Chemistry, Pergamon: New York, 1983; Chapter 6.
34. For examples, see: (a) Ent, H.; de Koning, H.; Speckamp, W. N. J. Org. Chem. 1986, 51, 1687. (b) Schoemaker, H. E.; Speckamp, W. N. Tetrahedron Lett. 1978, 1515. (c) Hart, D. J.; Kanai, K. J. Am. Chem. Soc. 1983, 103, 1255. For Prins cyclization, see: (d) Jaber, J. J.; Mitsui, K.; Rychnovsky, S. D. J. Org. Chem. 2001, 66, 4079. For related examples of stereoelectronic effects in the intermolecular addition of nucleophiles to iminium ions, see: (e) Heathcock, C. H.; Kleinman, E. F.; Binkley, E. S. J. Am. Chem. Soc. 1982, 104, 1054. (f) Demailly, G.; Solladié, G. J. Org. Chem. 1981, 46, 3102. (g) Overman, L. E.; Freerks, R. L. J. Org. Chem. 1981, 46, 6, 2833. (h) Overman, L. E.; Fukaya, C. J. Am. Chem. Soc. 1980, 102, 1454. (i) Stevens, R. V.; Lee, A. W. M. J. Am. Chem. Soc. 1979, 101, 7032. (j) Wenkert, E.; Chang, C.-J.; Chawla, H. P. S.; Cochran, D. W.; Hagaman, E. W.; King, J. C.; Orito, K. J. Am. Chem. Soc. 1976, 98, 3645. (k) Ziegler, F. E.; Spitzner, E. B. J. Am. Chem. Soc. 1973, 95, 7146. (l) Deslongchamps, P. Stereoelectronic Effects in Organic Chemistry, Pergamon: New York, 1983; Chapter 6.
35. For examples, see: (a) Ent, H.; de Koning, H.; Speckamp, W. N. J. Org. Chem. 1986, 51, 1687. (b) Schoemaker, H. E.; Speckamp, W. N. Tetrahedron Lett. 1978, 1515. (c) Hart, D. J.; Kanai, K. J. Am. Chem. Soc. 1983, 103, 1255. For Prins cyclization, see: (d) Jaber, J. J.; Mitsui, K.; Rychnovsky, S. D. J. Org. Chem. 2001, 66, 4079. For related examples of stereoelectronic effects in the intermolecular addition of nucleophiles to iminium ions, see: (e) Heathcock, C. H.; Kleinman, E. F.; Binkley, E. S. J. Am. Chem. Soc. 1982, 104, 1054. (f) Demailly, G.; Solladié, G. J. Org. Chem. 1981, 46, 3102. (g) Overman, L. E.; Freerks, R. L. J. Org. Chem. 1981, 46, 6, 2833. (h) Overman, L. E.; Fukaya, C. J. Am. Chem. Soc. 1980, 102, 1454. (i) Stevens, R. V.; Lee, A. W. M. J. Am. Chem. Soc. 1979, 101, 7032. (j) Wenkert, E.; Chang, C.-J.; Chawla, H. P. S.; Cochran, D. W.; Hagaman, E. W.; King, J. C.; Orito, K. J. Am. Chem. Soc. 1976, 98, 3645. (k) Ziegler, F. E.; Spitzner, E. B. J. Am. Chem. Soc. 1973, 95, 7146. (l) Deslongchamps, P. Stereoelectronic Effects in Organic Chemistry, Pergamon: New York, 1983; Chapter 6.
36. For examples, see: (a) Ent, H.; de Koning, H.; Speckamp, W. N. J. Org. Chem. 1986, 51, 1687. (b) Schoemaker, H. E.; Speckamp, W. N. Tetrahedron Lett. 1978, 1515. (c) Hart, D. J.; Kanai, K. J. Am. Chem. Soc. 1983, 103, 1255. For Prins cyclization, see: (d) Jaber, J. J.; Mitsui, K.; Rychnovsky, S. D. J. Org. Chem. 2001, 66, 4079. For related examples of stereoelectronic effects in the intermolecular addition of nucleophiles to iminium ions, see: (e) Heathcock, C. H.; Kleinman, E. F.; Binkley, E. S. J. Am. Chem. Soc. 1982, 104, 1054. (f) Demailly, G.; Solladié, G. J. Org. Chem. 1981, 46, 3102. (g) Overman, L. E.; Freerks, R. L. J. Org. Chem. 1981, 46, 6, 2833. (h) Overman, L. E.; Fukaya, C. J. Am. Chem. Soc. 1980, 102, 1454. (i) Stevens, R. V.; Lee, A. W. M. J. Am. Chem. Soc. 1979, 101, 7032. (j) Wenkert, E.; Chang, C.-J.; Chawla, H. P. S.; Cochran, D. W.; Hagaman, E. W.; King, J. C.; Orito, K. J. Am. Chem. Soc. 1976, 98, 3645. (k) Ziegler, F. E.; Spitzner, E. B. J. Am. Chem. Soc. 1973, 95, 7146. (l) Deslongchamps, P. Stereoelectronic Effects in Organic Chemistry, Pergamon: New York, 1983; Chapter 6.
37. For examples, see: (a) Ent, H.; de Koning, H.; Speckamp, W. N. J. Org. Chem. 1986, 51, 1687. (b) Schoemaker, H. E.; Speckamp, W. N. Tetrahedron Lett. 1978, 1515. (c) Hart, D. J.; Kanai, K. J. Am. Chem. Soc. 1983, 103, 1255. For Prins cyclization, see: (d) Jaber, J. J.; Mitsui, K.; Rychnovsky, S. D. J. Org. Chem. 2001, 66, 4079. For related examples of stereoelectronic effects in the intermolecular addition of nucleophiles to iminium ions, see: (e) Heathcock, C. H.; Kleinman, E. F.; Binkley, E. S. J. Am. Chem. Soc. 1982, 104, 1054. (f) Demailly, G.; Solladié, G. J. Org. Chem. 1981, 46, 3102. (g) Overman, L. E.; Freerks, R. L. J. Org. Chem. 1981, 46, 6, 2833. (h) Overman, L. E.; Fukaya, C. J. Am. Chem. Soc. 1980, 102, 1454. (i) Stevens, R. V.; Lee, A. W. M. J. Am. Chem. Soc. 1979, 101, 7032. (j) Wenkert, E.; Chang, C.-J.; Chawla, H. P. S.; Cochran, D. W.; Hagaman, E. W.; King, J. C.; Orito, K. J. Am. Chem. Soc. 1976, 98, 3645. (k) Ziegler, F. E.; Spitzner, E. B. J. Am. Chem. Soc. 1973, 95, 7146. (l) Deslongchamps, P. Stereoelectronic Effects in Organic Chemistry, Pergamon: New York, 1983; Chapter 6.
38. For examples, see: (a) Ent, H.; de Koning, H.; Speckamp, W. N. J. Org. Chem. 1986, 51, 1687. (b) Schoemaker, H. E.; Speckamp, W. N. Tetrahedron Lett. 1978, 1515. (c) Hart, D. J.; Kanai, K. J. Am. Chem. Soc. 1983, 103, 1255. For Prins cyclization, see: (d) Jaber, J. J.; Mitsui, K.; Rychnovsky, S. D. J. Org. Chem. 2001, 66, 4079. For related examples of stereoelectronic effects in the intermolecular addition of nucleophiles to iminium ions, see: (e) Heathcock, C. H.; Kleinman, E. F.; Binkley, E. S. J. Am. Chem. Soc. 1982, 104, 1054. (f) Demailly, G.; Solladié, G. J. Org. Chem. 1981, 46, 3102. (g) Overman, L. E.; Freerks, R. L. J. Org. Chem. 1981, 46, 6, 2833. (h) Overman, L. E.; Fukaya, C. J. Am. Chem. Soc. 1980, 102, 1454. (i) Stevens, R. V.; Lee, A. W. M. J. Am. Chem. Soc. 1979, 101, 7032. (j) Wenkert, E.; Chang, C.-J.; Chawla, H. P. S.; Cochran, D. W.; Hagaman, E. W.; King, J. C.; Orito, K. J. Am. Chem. Soc. 1976, 98, 3645. (k) Ziegler, F. E.; Spitzner, E. B. J. Am. Chem. Soc. 1973, 95, 7146. (l) Deslongchamps, P. Stereoelectronic Effects in Organic Chemistry, Pergamon: New York, 1983; Chapter 6.
39. For examples, see: (a) Ent, H.; de Koning, H.; Speckamp, W. N. J. Org. Chem. 1986, 51, 1687. (b) Schoemaker, H. E.; Speckamp, W. N. Tetrahedron Lett. 1978, 1515. (c) Hart, D. J.; Kanai, K. J. Am. Chem. Soc. 1983, 103, 1255. For Prins cyclization, see: (d) Jaber, J. J.; Mitsui, K.; Rychnovsky, S. D. J. Org. Chem. 2001, 66, 4079. For related examples of stereoelectronic effects in the intermolecular addition of nucleophiles to iminium ions, see: (e) Heathcock, C. H.; Kleinman, E. F.; Binkley, E. S. J. Am. Chem. Soc. 1982, 104, 1054. (f) Demailly, G.; Solladié, G. J. Org. Chem. 1981, 46, 3102. (g) Overman, L. E.; Freerks, R. L. J. Org. Chem. 1981, 46, 6, 2833. (h) Overman, L. E.; Fukaya, C. J. Am. Chem. Soc. 1980, 102, 1454. (i) Stevens, R. V.; Lee, A. W. M. J. Am. Chem. Soc. 1979, 101, 7032. (j) Wenkert, E.; Chang, C.-J.; Chawla, H. P. S.; Cochran, D. W.; Hagaman, E. W.; King, J. C.; Orito, K. J. Am. Chem. Soc. 1976, 98, 3645. (k) Ziegler, F. E.; Spitzner, E. B. J. Am. Chem. Soc. 1973, 95, 7146. (l) Deslongchamps, P. Stereoelectronic Effects in Organic Chemistry, Pergamon: New York, 1983; Chapter 6.
40. For examples, see: (a) Ent, H.; de Koning, H.; Speckamp, W. N. J. Org. Chem. 1986, 51, 1687. (b) Schoemaker, H. E.; Speckamp, W. N. Tetrahedron Lett. 1978, 1515. (c) Hart, D. J.; Kanai, K. J. Am. Chem. Soc. 1983, 103, 1255. For Prins cyclization, see: (d) Jaber, J. J.; Mitsui, K.; Rychnovsky, S. D. J. Org. Chem. 2001, 66, 4079. For related examples of stereoelectronic effects in the intermolecular addition of nucleophiles to iminium ions, see: (e) Heathcock, C. H.; Kleinman, E. F.; Binkley, E. S. J. Am. Chem. Soc. 1982, 104, 1054. (f) Demailly, G.; Solladié, G. J. Org. Chem. 1981, 46, 3102. (g) Overman, L. E.; Freerks, R. L. J. Org. Chem. 1981, 46, 6, 2833. (h) Overman, L. E.; Fukaya, C. J. Am. Chem. Soc. 1980, 102, 1454. (i) Stevens, R. V.; Lee, A. W. M. J. Am. Chem. Soc. 1979, 101, 7032. (j) Wenkert, E.; Chang, C.-J.; Chawla, H. P. S.; Cochran, D. W.; Hagaman, E. W.; King, J. C.; Orito, K. J. Am. Chem. Soc. 1976, 98, 3645. (k) Ziegler, F. E.; Spitzner, E. B. J. Am. Chem. Soc. 1973, 95, 7146. (l) Deslongchamps, P. Stereoelectronic Effects in Organic Chemistry, Pergamon: New York, 1983; Chapter 6.
41. For examples, see: (a) Ent, H.; de Koning, H.; Speckamp, W. N. J. Org. Chem. 1986, 51, 1687. (b) Schoemaker, H. E.; Speckamp, W. N. Tetrahedron Lett. 1978, 1515. (c) Hart, D. J.; Kanai, K. J. Am. Chem. Soc. 1983, 103, 1255. For Prins cyclization, see: (d) Jaber, J. J.; Mitsui, K.; Rychnovsky, S. D. J. Org. Chem. 2001, 66, 4079. For related examples of stereoelectronic effects in the intermolecular addition of nucleophiles to iminium ions, see: (e) Heathcock, C. H.; Kleinman, E. F.; Binkley, E. S. J. Am. Chem. Soc. 1982, 104, 1054. (f) Demailly, G.; Solladié, G. J. Org. Chem. 1981, 46, 3102. (g) Overman, L. E.; Freerks, R. L. J. Org. Chem. 1981, 46, 6, 2833. (h) Overman, L. E.; Fukaya, C. J. Am. Chem. Soc. 1980, 102, 1454. (i) Stevens, R. V.; Lee, A. W. M. J. Am. Chem. Soc. 1979, 101, 7032. (j) Wenkert, E.; Chang, C.-J.; Chawla, H. P. S.; Cochran, D. W.; Hagaman, E. W.; King, J. C.; Orito, K. J. Am. Chem. Soc. 1976, 98, 3645. (k) Ziegler, F. E.; Spitzner, E. B. J. Am. Chem. Soc. 1973, 95, 7146. (l) Deslongchamps, P. Stereoelectronic Effects in Organic Chemistry, Pergamon: New York, 1983; Chapter 6.
42. For examples, see: (a) Ent, H.; de Koning, H.; Speckamp, W. N. J. Org. Chem. 1986, 51, 1687. (b) Schoemaker, H. E.; Speckamp, W. N. Tetrahedron Lett. 1978, 1515. (c) Hart, D. J.; Kanai, K. J. Am. Chem. Soc. 1983, 103, 1255. For Prins cyclization, see: (d) Jaber, J. J.; Mitsui, K.; Rychnovsky, S. D. J. Org. Chem. 2001, 66, 4079. For related examples of stereoelectronic effects in the intermolecular addition of nucleophiles to iminium ions, see: (e) Heathcock, C. H.; Kleinman, E. F.; Binkley, E. S. J. Am. Chem. Soc. 1982, 104, 1054. (f) Demailly, G.; Solladié, G. J. Org. Chem. 1981, 46, 3102. (g) Overman, L. E.; Freerks, R. L. J. Org. Chem. 1981, 46, 6, 2833. (h) Overman, L. E.; Fukaya, C. J. Am. Chem. Soc. 1980, 102, 1454. (i) Stevens, R. V.; Lee, A. W. M. J. Am. Chem. Soc. 1979, 101, 7032. (j) Wenkert, E.; Chang, C.-J.; Chawla, H. P. S.; Cochran, D. W.; Hagaman, E. W.; King, J. C.; Orito, K. J. Am. Chem. Soc. 1976, 98, 3645. (k) Ziegler, F. E.; Spitzner, E. B. J. Am. Chem. Soc. 1973, 95, 7146. (l) Deslongchamps, P. Stereoelectronic Effects in Organic Chemistry, Pergamon: New York, 1983; Chapter 6.
43. For authoritative reviews, see: (a) Maryanoff, B. E.; Zhang, H.-C.; Cohen, J. H.; Turchi, I. J.; Maryanoff, C. A. Chem. Rev. 2004, 104, 1431. (b) Royer, J.; Bonin, M.; Micouin, J. Chem. Rev. 2004, 104, 2311. (c) Speckamp, W. N.; Moolenaar, M. J. Tetrahedron 2000, 56, 3817. (d) Hiemstra, H.; Speckamp, W. N. In Comprehensive Organic Synthesis; Trost, B. M., Fleming, I., Heathcock, C. H., Eds.; Pergamon: New York, 1991, 2, 1047. (e) Speckamp, W. N.; Hiemstra, H. Tetrahedron 1985, 41, 4367. (f) Speckamp, W. N. Recl. Trav. Chim. Pays-Bas 1981, 100, 345.
44. For authoritative reviews, see: (a) Maryanoff, B. E.; Zhang, H.-C.; Cohen, J. H.; Turchi, I. J.; Maryanoff, C. A. Chem. Rev. 2004, 104, 1431. (b) Royer, J.; Bonin, M.; Micouin, J. Chem. Rev. 2004, 104, 2311. (c) Speckamp, W. N.; Moolenaar, M. J. Tetrahedron 2000, 56, 3817. (d) Hiemstra, H.; Speckamp, W. N. In Comprehensive Organic Synthesis; Trost, B. M., Fleming, I., Heathcock, C. H., Eds.; Pergamon: New York, 1991, 2, 1047. (e) Speckamp, W. N.; Hiemstra, H. Tetrahedron 1985, 41, 4367. (f) Speckamp, W. N. Recl. Trav. Chim. Pays-Bas 1981, 100, 345.
45. For authoritative reviews, see: (a) Maryanoff, B. E.; Zhang, H.-C.; Cohen, J. H.; Turchi, I. J.; Maryanoff, C. A. Chem. Rev. 2004, 104, 1431. (b) Royer, J.; Bonin, M.; Micouin, J. Chem. Rev. 2004, 104, 2311. (c) Speckamp, W. N.; Moolenaar, M. J. Tetrahedron 2000, 56, 3817. (d) Hiemstra, H.; Speckamp, W. N. In Comprehensive Organic Synthesis; Trost, B. M., Fleming, I., Heathcock, C. H., Eds.; Pergamon: New York, 1991, 2, 1047. (e) Speckamp, W. N.; Hiemstra, H. Tetrahedron 1985, 41, 4367. (f) Speckamp, W. N. Recl. Trav. Chim. Pays-Bas 1981, 100, 345.
46. For authoritative reviews, see: (a) Maryanoff, B. E.; Zhang, H.-C.; Cohen, J. H.; Turchi, I. J.; Maryanoff, C. A. Chem. Rev. 2004, 104, 1431. (b) Royer, J.; Bonin, M.; Micouin, J. Chem. Rev. 2004, 104, 2311. (c) Speckamp, W. N.; Moolenaar, M. J. Tetrahedron 2000, 56, 3817. (d) Hiemstra, H.; Speckamp, W. N. In Comprehensive Organic Synthesis; Trost, B. M., Fleming, I., Heathcock, C. H., Eds.; Pergamon: New York, 1991, 2, 1047. (e) Speckamp, W. N.; Hiemstra, H. Tetrahedron 1985, 41, 4367. (f) Speckamp, W. N. Recl. Trav. Chim. Pays-Bas 1981, 100, 345.
47. For authoritative reviews, see: (a) Maryanoff, B. E.; Zhang, H.-C.; Cohen, J. H.; Turchi, I. J.; Maryanoff, C. A. Chem. Rev. 2004, 104, 1431. (b) Royer, J.; Bonin, M.; Micouin, J. Chem. Rev. 2004, 104, 2311. (c) Speckamp, W. N.; Moolenaar, M. J. Tetrahedron 2000, 56, 3817. (d) Hiemstra, H.; Speckamp, W. N. In Comprehensive Organic Synthesis; Trost, B. M., Fleming, I., Heathcock, C. H., Eds.; Pergamon: New York, 1991, 2, 1047. (e) Speckamp, W. N.; Hiemstra, H. Tetrahedron 1985, 41, 4367. (f) Speckamp, W. N. Recl. Trav. Chim. Pays-Bas 1981, 100, 345.
48. For authoritative reviews, see: (a) Maryanoff, B. E.; Zhang, H.-C.; Cohen, J. H.; Turchi, I. J.; Maryanoff, C. A. Chem. Rev. 2004, 104, 1431. (b) Royer, J.; Bonin, M.; Micouin, J. Chem. Rev. 2004, 104, 2311. (c) Speckamp, W. N.; Moolenaar, M. J. Tetrahedron 2000, 56, 3817. (d) Hiemstra, H.; Speckamp, W. N. In Comprehensive Organic Synthesis; Trost, B. M., Fleming, I., Heathcock, C. H., Eds.; Pergamon: New York, 1991, 2, 1047. (e) Speckamp, W. N.; Hiemstra, H. Tetrahedron 1985, 41, 4367. (f) Speckamp, W. N. Recl. Trav. Chim. Pays-Bas 1981, 100, 345.
49. Analogy with Stork - Eschenmoser proposals for polyene cyclizations has been made; see: (a) Hiemstra, H.; Sno, M. H. A. M.; Vijn, R. J.; Speckamp, W. N. J. Org. Chem. 1985, 50, 4014. (b) Stork, G.; Burgstahler, A. W. J. Am. Chem. Soc. 1955, 77, 5068. (c) Eschenmoser, A.; Ruzicka, L.; Jeger, O.; Arigoni, D. Helv. Chim. Acta 1955, 38, 1890.
50. Analogy with Stork - Eschenmoser proposals for polyene cyclizations has been made; see: (a) Hiemstra, H.; Sno, M. H. A. M.; Vijn, R. J.; Speckamp, W. N. J. Org. Chem. 1985, 50, 4014. (b) Stork, G.; Burgstahler, A. W. J. Am. Chem. Soc. 1955, 77, 5068. (c) Eschenmoser, A.; Ruzicka, L.; Jeger, O.; Arigoni, D. Helv. Chim. Acta 1955, 38, 1890.
51. Analogy with Stork - Eschenmoser proposals for polyene cyclizations has been made; see: (a) Hiemstra, H.; Sno, M. H. A. M.; Vijn, R. J.; Speckamp, W. N. J. Org. Chem. 1985, 50, 4014. (b) Stork, G.; Burgstahler, A. W. J. Am. Chem. Soc. 1955, 77, 5068. (c) Eschenmoser, A.; Ruzicka, L.; Jeger, O.; Arigoni, D. Helv. Chim. Acta 1955, 38, 1890.
52. For an early example, see: Dijkink, J.; Schoemaker, H. E.; Speckamp, W. N. Tetrahedron Lett. 1975, 4043.
53. Fisher, M. J.; Overman, L. E. J. Org. Chem. 1990, 55, 1447.
54. For a recent example, see: Beyersbergen van Henegouwen, W. G.; Hiemstra, H. J. Org. Chem. 1997, 62, 8862 and references therein.
55. Hanessian, S.; Margarita, R. Tetrahedron Lett. 1998, 39, 5887.
56. For examples of cyclic vinyl cations, see: (a) Pellicciari, R.; Natalini, B.; Sadeghpour, B. M.; Marinozzi, M.; Snyder, J. P.; Williamson, B. L.; Kuethe, J. T.; Padwa, A. J. Am. Chem. Soc. 1996, 118, 1. (b) Balog, A.; Curran D. P. J. Org. Chem. 1995, 60, 337. (c) Johnson, W. S.; Yarnell, T. M.; Myers, R. F.; Morton, D. R. Tetrahedron Lett. 1978, 2549. (d) Kozar, L. G.; Clark, R. D.; Heathcock, C. H. J. Org. Chem. 1977, 42, 1386. (e) Schleyer, P. V. R.; Pfeifer, W. D.; Bahn, C. A.; Bocher, S.; Harding, C. E.; Hummel, K.; Hanack, M.; Stang, P. J. J. Am. Chem. Soc. 1971, 93, 1513. (f) Peterson, P. E.; Kamat R. J. J. Am. Chem. Soc. 1969, 91, 4521. For reviews on vinyl cations, see: (g) Nefedov, V. D.; Sinotova, E. N.; Lebedev, V. P. Russ. Chem. Rev. 1992, 61, 283. (h) Stang, P. J.; Rappoport, Z.; Hanack, M.; Subramanian, L. B. Vinyl Cations; Academic Press: New York, 1979. (i) Stang, P, J. Acc. Chem. Res. 1978, 11, 107. (j) Hanack, M. Angew. Chem., Int. Ed. Engl. 1978, 17, 333. (k) Rappoport, Z. Acc. Chem. Res. 1976, 9, 265.
57. For examples of cyclic vinyl cations, see: (a) Pellicciari, R.; Natalini, B.; Sadeghpour, B. M.; Marinozzi, M.; Snyder, J. P.; Williamson, B. L.; Kuethe, J. T.; Padwa, A. J. Am. Chem. Soc. 1996, 118, 1. (b) Balog, A.; Curran D. P. J. Org. Chem. 1995, 60, 337. (c) Johnson, W. S.; Yarnell, T. M.; Myers, R. F.; Morton, D. R. Tetrahedron Lett. 1978, 2549. (d) Kozar, L. G.; Clark, R. D.; Heathcock, C. H. J. Org. Chem. 1977, 42, 1386. (e) Schleyer, P. V. R.; Pfeifer, W. D.; Bahn, C. A.; Bocher, S.; Harding, C. E.; Hummel, K.; Hanack, M.; Stang, P. J. J. Am. Chem. Soc. 1971, 93, 1513. (f) Peterson, P. E.; Kamat R. J. J. Am. Chem. Soc. 1969, 91, 4521. For reviews on vinyl cations, see: (g) Nefedov, V. D.; Sinotova, E. N.; Lebedev, V. P. Russ. Chem. Rev. 1992, 61, 283. (h) Stang, P. J.; Rappoport, Z.; Hanack, M.; Subramanian, L. B. Vinyl Cations; Academic Press: New York, 1979. (i) Stang, P, J. Acc. Chem. Res. 1978, 11, 107. (j) Hanack, M. Angew. Chem., Int. Ed. Engl. 1978, 17, 333. (k) Rappoport, Z. Acc. Chem. Res. 1976, 9, 265.
58. For examples of cyclic vinyl cations, see: (a) Pellicciari, R.; Natalini, B.; Sadeghpour, B. M.; Marinozzi, M.; Snyder, J. P.; Williamson, B. L.; Kuethe, J. T.; Padwa, A. J. Am. Chem. Soc. 1996, 118, 1. (b) Balog, A.; Curran D. P. J. Org. Chem. 1995, 60, 337. (c) Johnson, W. S.; Yarnell, T. M.; Myers, R. F.; Morton, D. R. Tetrahedron Lett. 1978, 2549. (d) Kozar, L. G.; Clark, R. D.; Heathcock, C. H. J. Org. Chem. 1977, 42, 1386. (e) Schleyer, P. V. R.; Pfeifer, W. D.; Bahn, C. A.; Bocher, S.; Harding, C. E.; Hummel, K.; Hanack, M.; Stang, P. J. J. Am. Chem. Soc. 1971, 93, 1513. (f) Peterson, P. E.; Kamat R. J. J. Am. Chem. Soc. 1969, 91, 4521. For reviews on vinyl cations, see: (g) Nefedov, V. D.; Sinotova, E. N.; Lebedev, V. P. Russ. Chem. Rev. 1992, 61, 283. (h) Stang, P. J.; Rappoport, Z.; Hanack, M.; Subramanian, L. B. Vinyl Cations; Academic Press: New York, 1979. (i) Stang, P, J. Acc. Chem. Res. 1978, 11, 107. (j) Hanack, M. Angew. Chem., Int. Ed. Engl. 1978, 17, 333. (k) Rappoport, Z. Acc. Chem. Res. 1976, 9, 265.
59. For examples of cyclic vinyl cations, see: (a) Pellicciari, R.; Natalini, B.; Sadeghpour, B. M.; Marinozzi, M.; Snyder, J. P.; Williamson, B. L.; Kuethe, J. T.; Padwa, A. J. Am. Chem. Soc. 1996, 118, 1. (b) Balog, A.; Curran D. P. J. Org. Chem. 1995, 60, 337. (c) Johnson, W. S.; Yarnell, T. M.; Myers, R. F.; Morton, D. R. Tetrahedron Lett. 1978, 2549. (d) Kozar, L. G.; Clark, R. D.; Heathcock, C. H. J. Org. Chem. 1977, 42, 1386. (e) Schleyer, P. V. R.; Pfeifer, W. D.; Bahn, C. A.; Bocher, S.; Harding, C. E.; Hummel, K.; Hanack, M.; Stang, P. J. J. Am. Chem. Soc. 1971, 93, 1513. (f) Peterson, P. E.; Kamat R. J. J. Am. Chem. Soc. 1969, 91, 4521. For reviews on vinyl cations, see: (g) Nefedov, V. D.; Sinotova, E. N.; Lebedev, V. P. Russ. Chem. Rev. 1992, 61, 283. (h) Stang, P. J.; Rappoport, Z.; Hanack, M.; Subramanian, L. B. Vinyl Cations; Academic Press: New York, 1979. (i) Stang, P, J. Acc. Chem. Res. 1978, 11, 107. (j) Hanack, M. Angew. Chem., Int. Ed. Engl. 1978, 17, 333. (k) Rappoport, Z. Acc. Chem. Res. 1976, 9, 265.
60. For examples of cyclic vinyl cations, see: (a) Pellicciari, R.; Natalini, B.; Sadeghpour, B. M.; Marinozzi, M.; Snyder, J. P.; Williamson, B. L.; Kuethe, J. T.; Padwa, A. J. Am. Chem. Soc. 1996, 118, 1. (b) Balog, A.; Curran D. P. J. Org. Chem. 1995, 60, 337. (c) Johnson, W. S.; Yarnell, T. M.; Myers, R. F.; Morton, D. R. Tetrahedron Lett. 1978, 2549. (d) Kozar, L. G.; Clark, R. D.; Heathcock, C. H. J. Org. Chem. 1977, 42, 1386. (e) Schleyer, P. V. R.; Pfeifer, W. D.; Bahn, C. A.; Bocher, S.; Harding, C. E.; Hummel, K.; Hanack, M.; Stang, P. J. J. Am. Chem. Soc. 1971, 93, 1513. (f) Peterson, P. E.; Kamat R. J. J. Am. Chem. Soc. 1969, 91, 4521. For reviews on vinyl cations, see: (g) Nefedov, V. D.; Sinotova, E. N.; Lebedev, V. P. Russ. Chem. Rev. 1992, 61, 283. (h) Stang, P. J.; Rappoport, Z.; Hanack, M.; Subramanian, L. B. Vinyl Cations; Academic Press: New York, 1979. (i) Stang, P, J. Acc. Chem. Res. 1978, 11, 107. (j) Hanack, M. Angew. Chem., Int. Ed. Engl. 1978, 17, 333. (k) Rappoport, Z. Acc. Chem. Res. 1976, 9, 265.
61. For examples of cyclic vinyl cations, see: (a) Pellicciari, R.; Natalini, B.; Sadeghpour, B. M.; Marinozzi, M.; Snyder, J. P.; Williamson, B. L.; Kuethe, J. T.; Padwa, A. J. Am. Chem. Soc. 1996, 118, 1. (b) Balog, A.; Curran D. P. J. Org. Chem. 1995, 60, 337. (c) Johnson, W. S.; Yarnell, T. M.; Myers, R. F.; Morton, D. R. Tetrahedron Lett. 1978, 2549. (d) Kozar, L. G.; Clark, R. D.; Heathcock, C. H. J. Org. Chem. 1977, 42, 1386. (e) Schleyer, P. V. R.; Pfeifer, W. D.; Bahn, C. A.; Bocher, S.; Harding, C. E.; Hummel, K.; Hanack, M.; Stang, P. J. J. Am. Chem. Soc. 1971, 93, 1513. (f) Peterson, P. E.; Kamat R. J. J. Am. Chem. Soc. 1969, 91, 4521. For reviews on vinyl cations, see: (g) Nefedov, V. D.; Sinotova, E. N.; Lebedev, V. P. Russ. Chem. Rev. 1992, 61, 283. (h) Stang, P. J.; Rappoport, Z.; Hanack, M.; Subramanian, L. B. Vinyl Cations; Academic Press: New York, 1979. (i) Stang, P, J. Acc. Chem. Res. 1978, 11, 107. (j) Hanack, M. Angew. Chem., Int. Ed. Engl. 1978, 17, 333. (k) Rappoport, Z. Acc. Chem. Res. 1976, 9, 265.
62. For examples of cyclic vinyl cations, see: (a) Pellicciari, R.; Natalini, B.; Sadeghpour, B. M.; Marinozzi, M.; Snyder, J. P.; Williamson, B. L.; Kuethe, J. T.; Padwa, A. J. Am. Chem. Soc. 1996, 118, 1. (b) Balog, A.; Curran D. P. J. Org. Chem. 1995, 60, 337. (c) Johnson, W. S.; Yarnell, T. M.; Myers, R. F.; Morton, D. R. Tetrahedron Lett. 1978, 2549. (d) Kozar, L. G.; Clark, R. D.; Heathcock, C. H. J. Org. Chem. 1977, 42, 1386. (e) Schleyer, P. V. R.; Pfeifer, W. D.; Bahn, C. A.; Bocher, S.; Harding, C. E.; Hummel, K.; Hanack, M.; Stang, P. J. J. Am. Chem. Soc. 1971, 93, 1513. (f) Peterson, P. E.; Kamat R. J. J. Am. Chem. Soc. 1969, 91, 4521. For reviews on vinyl cations, see: (g) Nefedov, V. D.; Sinotova, E. N.; Lebedev, V. P. Russ. Chem. Rev. 1992, 61, 283. (h) Stang, P. J.; Rappoport, Z.; Hanack, M.; Subramanian, L. B. Vinyl Cations; Academic Press: New York, 1979. (i) Stang, P, J. Acc. Chem. Res. 1978, 11, 107. (j) Hanack, M. Angew. Chem., Int. Ed. Engl. 1978, 17, 333. (k) Rappoport, Z. Acc. Chem. Res. 1976, 9, 265.
63. For examples of cyclic vinyl cations, see: (a) Pellicciari, R.; Natalini, B.; Sadeghpour, B. M.; Marinozzi, M.; Snyder, J. P.; Williamson, B. L.; Kuethe, J. T.; Padwa, A. J. Am. Chem. Soc. 1996, 118, 1. (b) Balog, A.; Curran D. P. J. Org. Chem. 1995, 60, 337. (c) Johnson, W. S.; Yarnell, T. M.; Myers, R. F.; Morton, D. R. Tetrahedron Lett. 1978, 2549. (d) Kozar, L. G.; Clark, R. D.; Heathcock, C. H. J. Org. Chem. 1977, 42, 1386. (e) Schleyer, P. V. R.; Pfeifer, W. D.; Bahn, C. A.; Bocher, S.; Harding, C. E.; Hummel, K.; Hanack, M.; Stang, P. J. J. Am. Chem. Soc. 1971, 93, 1513. (f) Peterson, P. E.; Kamat R. J. J. Am. Chem. Soc. 1969, 91, 4521. For reviews on vinyl cations, see: (g) Nefedov, V. D.; Sinotova, E. N.; Lebedev, V. P. Russ. Chem. Rev. 1992, 61, 283. (h) Stang, P. J.; Rappoport, Z.; Hanack, M.; Subramanian, L. B. Vinyl Cations; Academic Press: New York, 1979. (i) Stang, P, J. Acc. Chem. Res. 1978, 11, 107. (j) Hanack, M. Angew. Chem., Int. Ed. Engl. 1978, 17, 333. (k) Rappoport, Z. Acc. Chem. Res. 1976, 9, 265.
64. For examples of cyclic vinyl cations, see: (a) Pellicciari, R.; Natalini, B.; Sadeghpour, B. M.; Marinozzi, M.; Snyder, J. P.; Williamson, B. L.; Kuethe, J. T.; Padwa, A. J. Am. Chem. Soc. 1996, 118, 1. (b) Balog, A.; Curran D. P. J. Org. Chem. 1995, 60, 337. (c) Johnson, W. S.; Yarnell, T. M.; Myers, R. F.; Morton, D. R. Tetrahedron Lett. 1978, 2549. (d) Kozar, L. G.; Clark, R. D.; Heathcock, C. H. J. Org. Chem. 1977, 42, 1386. (e) Schleyer, P. V. R.; Pfeifer, W. D.; Bahn, C. A.; Bocher, S.; Harding, C. E.; Hummel, K.; Hanack, M.; Stang, P. J. J. Am. Chem. Soc. 1971, 93, 1513. (f) Peterson, P. E.; Kamat R. J. J. Am. Chem. Soc. 1969, 91, 4521. For reviews on vinyl cations, see: (g) Nefedov, V. D.; Sinotova, E. N.; Lebedev, V. P. Russ. Chem. Rev. 1992, 61, 283. (h) Stang, P. J.; Rappoport, Z.; Hanack, M.; Subramanian, L. B. Vinyl Cations; Academic Press: New York, 1979. (i) Stang, P, J. Acc. Chem. Res. 1978, 11, 107. (j) Hanack, M. Angew. Chem., Int. Ed. Engl. 1978, 17, 333. (k) Rappoport, Z. Acc. Chem. Res. 1976, 9, 265.
65. For examples of cyclic vinyl cations, see: (a) Pellicciari, R.; Natalini, B.; Sadeghpour, B. M.; Marinozzi, M.; Snyder, J. P.; Williamson, B. L.; Kuethe, J. T.; Padwa, A. J. Am. Chem. Soc. 1996, 118, 1. (b) Balog, A.; Curran D. P. J. Org. Chem. 1995, 60, 337. (c) Johnson, W. S.; Yarnell, T. M.; Myers, R. F.; Morton, D. R. Tetrahedron Lett. 1978, 2549. (d) Kozar, L. G.; Clark, R. D.; Heathcock, C. H. J. Org. Chem. 1977, 42, 1386. (e) Schleyer, P. V. R.; Pfeifer, W. D.; Bahn, C. A.; Bocher, S.; Harding, C. E.; Hummel, K.; Hanack, M.; Stang, P. J. J. Am. Chem. Soc. 1971, 93, 1513. (f) Peterson, P. E.; Kamat R. J. J. Am. Chem. Soc. 1969, 91, 4521. For reviews on vinyl cations, see: (g) Nefedov, V. D.; Sinotova, E. N.; Lebedev, V. P. Russ. Chem. Rev. 1992, 61, 283. (h) Stang, P. J.; Rappoport, Z.; Hanack, M.; Subramanian, L. B. Vinyl Cations; Academic Press: New York, 1979. (i) Stang, P, J. Acc. Chem. Res. 1978, 11, 107. (j) Hanack, M. Angew. Chem., Int. Ed. Engl. 1978, 17, 333. (k) Rappoport, Z. Acc. Chem. Res. 1976, 9, 265.
66. For examples of cyclic vinyl cations, see: (a) Pellicciari, R.; Natalini, B.; Sadeghpour, B. M.; Marinozzi, M.; Snyder, J. P.; Williamson, B. L.; Kuethe, J. T.; Padwa, A. J. Am. Chem. Soc. 1996, 118, 1. (b) Balog, A.; Curran D. P. J. Org. Chem. 1995, 60, 337. (c) Johnson, W. S.; Yarnell, T. M.; Myers, R. F.; Morton, D. R. Tetrahedron Lett. 1978, 2549. (d) Kozar, L. G.; Clark, R. D.; Heathcock, C. H. J. Org. Chem. 1977, 42, 1386. (e) Schleyer, P. V. R.; Pfeifer, W. D.; Bahn, C. A.; Bocher, S.; Harding, C. E.; Hummel, K.; Hanack, M.; Stang, P. J. J. Am. Chem. Soc. 1971, 93, 1513. (f) Peterson, P. E.; Kamat R. J. J. Am. Chem. Soc. 1969, 91, 4521. For reviews on vinyl cations, see: (g) Nefedov, V. D.; Sinotova, E. N.; Lebedev, V. P. Russ. Chem. Rev. 1992, 61, 283. (h) Stang, P. J.; Rappoport, Z.; Hanack, M.; Subramanian, L. B. Vinyl Cations; Academic Press: New York, 1979. (i) Stang, P, J. Acc. Chem. Res. 1978, 11, 107. (j) Hanack, M. Angew. Chem., Int. Ed. Engl. 1978, 17, 333. (k) Rappoport, Z. Acc. Chem. Res. 1976, 9, 265.
67. Dewar, M. J. S.; Reynolds, C. H. J. Am. Chem. Soc. 1984, 106, 1744.
68. For examples of vinyl cation arylations, see: (a) Stang, P. J.; Anderson, A. G. J. Am. Chem. Soc. 1978, 100, 1520. (b) Roberts, R. M.; Abdel-Baset, M. B. J. Org. Chem. 1976, 41, 1698.
69. For examples of vinyl cation arylations, see: (a) Stang, P. J.; Anderson, A. G. J. Am. Chem. Soc. 1978, 100, 1520. (b) Roberts, R. M.; Abdel-Baset, M. B. J. Org. Chem. 1976, 41, 1698.
70. For recent examples of intramolecular Friedel - Crafts arylation of N-acyliminium ions, see: (a) Hanessian, S.; Papeo, G.; Angiolini, M.; Fettis, K.; Beretta, M.; Munro, A. J. Org. Chem. 2003, 68, 7204. (b) Luker, J.; Koot, W.-J.; Hiemstra, H.; Speckamp, W. N. J. Org. Chem. 1998, 63, 220. (c) Allin, S. M.; Northfield, C. J.; Page, M. I.; Slawin, A. M. Z. Tetrahedron Lett. 1998, 39, 4905. (d) Lee, Y. S.; Kang, D. W.; Lee, S. J.; Park, H. J. Org. Chem. 1995, 60, 7149. (e) Marson, C. M.; Pink, J. H.; Smith, C. Tetrahedron Lett. 1995, 36, 8107. (f) Robl, J. A.; Cimarusti, M. P.; Simpkins, L. M.; Weller, H. N.; Pan, Y. Y.; Malley, M.; DiMarco, J. D. J. Am. Chem. Soc. 1994, 116, 2348, (g) Bailey, P. D.; Morgan, K. M.; Smith, D. I.; Vernon, J. M. Tetrahedron Lett. 1994, 35, 7115. (h) Koot, W.-J.; Hiemstra, H.; Speckamp, W. N. Tetrahedron Lett. 1992, 33, 7969. (i) Kano, S.; Yuasa, Y.; Shibuya, S. Heterocydes 1985, 23, 365. (j) Maryanoff, B. E.; Molinari, A. J.; McComsey, D. F.; Maryanoff, C. A.; Wooden, G. P.; Olofson, R. A. J. Org. Chem. 1983, 48, 5074. See also ref 18a.
71. For recent examples of intramolecular Friedel - Crafts arylation of N-acyliminium ions, see: (a) Hanessian, S.; Papeo, G.; Angiolini, M.; Fettis, K.; Beretta, M.; Munro, A. J. Org. Chem. 2003, 68, 7204. (b) Luker, J.; Koot, W.-J.; Hiemstra, H.; Speckamp, W. N. J. Org. Chem. 1998, 63, 220. (c) Allin, S. M.; Northfield, C. J.; Page, M. I.; Slawin, A. M. Z. Tetrahedron Lett. 1998, 39, 4905. (d) Lee, Y. S.; Kang, D. W.; Lee, S. J.; Park, H. J. Org. Chem. 1995, 60, 7149. (e) Marson, C. M.; Pink, J. H.; Smith, C. Tetrahedron Lett. 1995, 36, 8107. (f) Robl, J. A.; Cimarusti, M. P.; Simpkins, L. M.; Weller, H. N.; Pan, Y. Y.; Malley, M.; DiMarco, J. D. J. Am. Chem. Soc. 1994, 116, 2348, (g) Bailey, P. D.; Morgan, K. M.; Smith, D. I.; Vernon, J. M. Tetrahedron Lett. 1994, 35, 7115. (h) Koot, W.-J.; Hiemstra, H.; Speckamp, W. N. Tetrahedron Lett. 1992, 33, 7969. (i) Kano, S.; Yuasa, Y.; Shibuya, S. Heterocydes 1985, 23, 365. (j) Maryanoff, B. E.; Molinari, A. J.; McComsey, D. F.; Maryanoff, C. A.; Wooden, G. P.; Olofson, R. A. J. Org. Chem. 1983, 48, 5074. See also ref 18a.
72. For recent examples of intramolecular Friedel - Crafts arylation of N-acyliminium ions, see: (a) Hanessian, S.; Papeo, G.; Angiolini, M.; Fettis, K.; Beretta, M.; Munro, A. J. Org. Chem. 2003, 68, 7204. (b) Luker, J.; Koot, W.-J.; Hiemstra, H.; Speckamp, W. N. J. Org. Chem. 1998, 63, 220. (c) Allin, S. M.; Northfield, C. J.; Page, M. I.; Slawin, A. M. Z. Tetrahedron Lett. 1998, 39, 4905. (d) Lee, Y. S.; Kang, D. W.; Lee, S. J.; Park, H. J. Org. Chem. 1995, 60, 7149. (e) Marson, C. M.; Pink, J. H.; Smith, C. Tetrahedron Lett. 1995, 36, 8107. (f) Robl, J. A.; Cimarusti, M. P.; Simpkins, L. M.; Weller, H. N.; Pan, Y. Y.; Malley, M.; DiMarco, J. D. J. Am. Chem. Soc. 1994, 116, 2348, (g) Bailey, P. D.; Morgan, K. M.; Smith, D. I.; Vernon, J. M. Tetrahedron Lett. 1994, 35, 7115. (h) Koot, W.-J.; Hiemstra, H.; Speckamp, W. N. Tetrahedron Lett. 1992, 33, 7969. (i) Kano, S.; Yuasa, Y.; Shibuya, S. Heterocydes 1985, 23, 365. (j) Maryanoff, B. E.; Molinari, A. J.; McComsey, D. F.; Maryanoff, C. A.; Wooden, G. P.; Olofson, R. A. J. Org. Chem. 1983, 48, 5074. See also ref 18a.
73. For recent examples of intramolecular Friedel - Crafts arylation of N-acyliminium ions, see: (a) Hanessian, S.; Papeo, G.; Angiolini, M.; Fettis, K.; Beretta, M.; Munro, A. J. Org. Chem. 2003, 68, 7204. (b) Luker, J.; Koot, W.-J.; Hiemstra, H.; Speckamp, W. N. J. Org. Chem. 1998, 63, 220. (c) Allin, S. M.; Northfield, C. J.; Page, M. I.; Slawin, A. M. Z. Tetrahedron Lett. 1998, 39, 4905. (d) Lee, Y. S.; Kang, D. W.; Lee, S. J.; Park, H. J. Org. Chem. 1995, 60, 7149. (e) Marson, C. M.; Pink, J. H.; Smith, C. Tetrahedron Lett. 1995, 36, 8107. (f) Robl, J. A.; Cimarusti, M. P.; Simpkins, L. M.; Weller, H. N.; Pan, Y. Y.; Malley, M.; DiMarco, J. D. J. Am. Chem. Soc. 1994, 116, 2348, (g) Bailey, P. D.; Morgan, K. M.; Smith, D. I.; Vernon, J. M. Tetrahedron Lett. 1994, 35, 7115. (h) Koot, W.-J.; Hiemstra, H.; Speckamp, W. N. Tetrahedron Lett. 1992, 33, 7969. (i) Kano, S.; Yuasa, Y.; Shibuya, S. Heterocydes 1985, 23, 365. (j) Maryanoff, B. E.; Molinari, A. J.; McComsey, D. F.; Maryanoff, C. A.; Wooden, G. P.; Olofson, R. A. J. Org. Chem. 1983, 48, 5074. See also ref 18a.
74. For recent examples of intramolecular Friedel - Crafts arylation of N-acyliminium ions, see: (a) Hanessian, S.; Papeo, G.; Angiolini, M.; Fettis, K.; Beretta, M.; Munro, A. J. Org. Chem. 2003, 68, 7204. (b) Luker, J.; Koot, W.-J.; Hiemstra, H.; Speckamp, W. N. J. Org. Chem. 1998, 63, 220. (c) Allin, S. M.; Northfield, C. J.; Page, M. I.; Slawin, A. M. Z. Tetrahedron Lett. 1998, 39, 4905. (d) Lee, Y. S.; Kang, D. W.; Lee, S. J.; Park, H. J. Org. Chem. 1995, 60, 7149. (e) Marson, C. M.; Pink, J. H.; Smith, C. Tetrahedron Lett. 1995, 36, 8107. (f) Robl, J. A.; Cimarusti, M. P.; Simpkins, L. M.; Weller, H. N.; Pan, Y. Y.; Malley, M.; DiMarco, J. D. J. Am. Chem. Soc. 1994, 116, 2348, (g) Bailey, P. D.; Morgan, K. M.; Smith, D. I.; Vernon, J. M. Tetrahedron Lett. 1994, 35, 7115. (h) Koot, W.-J.; Hiemstra, H.; Speckamp, W. N. Tetrahedron Lett. 1992, 33, 7969. (i) Kano, S.; Yuasa, Y.; Shibuya, S. Heterocydes 1985, 23, 365. (j) Maryanoff, B. E.; Molinari, A. J.; McComsey, D. F.; Maryanoff, C. A.; Wooden, G. P.; Olofson, R. A. J. Org. Chem. 1983, 48, 5074. See also ref 18a.
75. For recent examples of intramolecular Friedel - Crafts arylation of N-acyliminium ions, see: (a) Hanessian, S.; Papeo, G.; Angiolini, M.; Fettis, K.; Beretta, M.; Munro, A. J. Org. Chem. 2003, 68, 7204. (b) Luker, J.; Koot, W.-J.; Hiemstra, H.; Speckamp, W. N. J. Org. Chem. 1998, 63, 220. (c) Allin, S. M.; Northfield, C. J.; Page, M. I.; Slawin, A. M. Z. Tetrahedron Lett. 1998, 39, 4905. (d) Lee, Y. S.; Kang, D. W.; Lee, S. J.; Park, H. J. Org. Chem. 1995, 60, 7149. (e) Marson, C. M.; Pink, J. H.; Smith, C. Tetrahedron Lett. 1995, 36, 8107. (f) Robl, J. A.; Cimarusti, M. P.; Simpkins, L. M.; Weller, H. N.; Pan, Y. Y.; Malley, M.; DiMarco, J. D. J. Am. Chem. Soc. 1994, 116, 2348, (g) Bailey, P. D.; Morgan, K. M.; Smith, D. I.; Vernon, J. M. Tetrahedron Lett. 1994, 35, 7115. (h) Koot, W.-J.; Hiemstra, H.; Speckamp, W. N. Tetrahedron Lett. 1992, 33, 7969. (i) Kano, S.; Yuasa, Y.; Shibuya, S. Heterocydes 1985, 23, 365. (j) Maryanoff, B. E.; Molinari, A. J.; McComsey, D. F.; Maryanoff, C. A.; Wooden, G. P.; Olofson, R. A. J. Org. Chem. 1983, 48, 5074. See also ref 18a.
76. For recent examples of intramolecular Friedel - Crafts arylation of N-acyliminium ions, see: (a) Hanessian, S.; Papeo, G.; Angiolini, M.; Fettis, K.; Beretta, M.; Munro, A. J. Org. Chem. 2003, 68, 7204. (b) Luker, J.; Koot, W.-J.; Hiemstra, H.; Speckamp, W. N. J. Org. Chem. 1998, 63, 220. (c) Allin, S. M.; Northfield, C. J.; Page, M. I.; Slawin, A. M. Z. Tetrahedron Lett. 1998, 39, 4905. (d) Lee, Y. S.; Kang, D. W.; Lee, S. J.; Park, H. J. Org. Chem. 1995, 60, 7149. (e) Marson, C. M.; Pink, J. H.; Smith, C. Tetrahedron Lett. 1995, 36, 8107. (f) Robl, J. A.; Cimarusti, M. P.; Simpkins, L. M.; Weller, H. N.; Pan, Y. Y.; Malley, M.; DiMarco, J. D. J. Am. Chem. Soc. 1994, 116, 2348, (g) Bailey, P. D.; Morgan, K. M.; Smith, D. I.; Vernon, J. M. Tetrahedron Lett. 1994, 35, 7115. (h) Koot, W.-J.; Hiemstra, H.; Speckamp, W. N. Tetrahedron Lett. 1992, 33, 7969. (i) Kano, S.; Yuasa, Y.; Shibuya, S. Heterocydes 1985, 23, 365. (j) Maryanoff, B. E.; Molinari, A. J.; McComsey, D. F.; Maryanoff, C. A.; Wooden, G. P.; Olofson, R. A. J. Org. Chem. 1983, 48, 5074. See also ref 18a.
77. For recent examples of intramolecular Friedel - Crafts arylation of N-acyliminium ions, see: (a) Hanessian, S.; Papeo, G.; Angiolini, M.; Fettis, K.; Beretta, M.; Munro, A. J. Org. Chem. 2003, 68, 7204. (b) Luker, J.; Koot, W.-J.; Hiemstra, H.; Speckamp, W. N. J. Org. Chem. 1998, 63, 220. (c) Allin, S. M.; Northfield, C. J.; Page, M. I.; Slawin, A. M. Z. Tetrahedron Lett. 1998, 39, 4905. (d) Lee, Y. S.; Kang, D. W.; Lee, S. J.; Park, H. J. Org. Chem. 1995, 60, 7149. (e) Marson, C. M.; Pink, J. H.; Smith, C. Tetrahedron Lett. 1995, 36, 8107. (f) Robl, J. A.; Cimarusti, M. P.; Simpkins, L. M.; Weller, H. N.; Pan, Y. Y.; Malley, M.; DiMarco, J. D. J. Am. Chem. Soc. 1994, 116, 2348, (g) Bailey, P. D.; Morgan, K. M.; Smith, D. I.; Vernon, J. M. Tetrahedron Lett. 1994, 35, 7115. (h) Koot, W.-J.; Hiemstra, H.; Speckamp, W. N. Tetrahedron Lett. 1992, 33, 7969. (i) Kano, S.; Yuasa, Y.; Shibuya, S. Heterocydes 1985, 23, 365. (j) Maryanoff, B. E.; Molinari, A. J.; McComsey, D. F.; Maryanoff, C. A.; Wooden, G. P.; Olofson, R. A. J. Org. Chem. 1983, 48, 5074. See also ref 18a.
78. For recent examples of intramolecular Friedel - Crafts arylation of N-acyliminium ions, see: (a) Hanessian, S.; Papeo, G.; Angiolini, M.; Fettis, K.; Beretta, M.; Munro, A. J. Org. Chem. 2003, 68, 7204. (b) Luker, J.; Koot, W.-J.; Hiemstra, H.; Speckamp, W. N. J. Org. Chem. 1998, 63, 220. (c) Allin, S. M.; Northfield, C. J.; Page, M. I.; Slawin, A. M. Z. Tetrahedron Lett. 1998, 39, 4905. (d) Lee, Y. S.; Kang, D. W.; Lee, S. J.; Park, H. J. Org. Chem. 1995, 60, 7149. (e) Marson, C. M.; Pink, J. H.; Smith, C. Tetrahedron Lett. 1995, 36, 8107. (f) Robl, J. A.; Cimarusti, M. P.; Simpkins, L. M.; Weller, H. N.; Pan, Y. Y.; Malley, M.; DiMarco, J. D. J. Am. Chem. Soc. 1994, 116, 2348, (g) Bailey, P. D.; Morgan, K. M.; Smith, D. I.; Vernon, J. M. Tetrahedron Lett. 1994, 35, 7115. (h) Koot, W.-J.; Hiemstra, H.; Speckamp, W. N. Tetrahedron Lett. 1992, 33, 7969. (i) Kano, S.; Yuasa, Y.; Shibuya, S. Heterocydes 1985, 23, 365. (j) Maryanoff, B. E.; Molinari, A. J.; McComsey, D. F.; Maryanoff, C. A.; Wooden, G. P.; Olofson, R. A. J. Org. Chem. 1983, 48, 5074. See also ref 18a.
79. For recent examples of intramolecular Friedel - Crafts arylation of N-acyliminium ions, see: (a) Hanessian, S.; Papeo, G.; Angiolini, M.; Fettis, K.; Beretta, M.; Munro, A. J. Org. Chem. 2003, 68, 7204. (b) Luker, J.; Koot, W.-J.; Hiemstra, H.; Speckamp, W. N. J. Org. Chem. 1998, 63, 220. (c) Allin, S. M.; Northfield, C. J.; Page, M. I.; Slawin, A. M. Z. Tetrahedron Lett. 1998, 39, 4905. (d) Lee, Y. S.; Kang, D. W.; Lee, S. J.; Park, H. J. Org. Chem. 1995, 60, 7149. (e) Marson, C. M.; Pink, J. H.; Smith, C. Tetrahedron Lett. 1995, 36, 8107. (f) Robl, J. A.; Cimarusti, M. P.; Simpkins, L. M.; Weller, H. N.; Pan, Y. Y.; Malley, M.; DiMarco, J. D. J. Am. Chem. Soc. 1994, 116, 2348, (g) Bailey, P. D.; Morgan, K. M.; Smith, D. I.; Vernon, J. M. Tetrahedron Lett. 1994, 35, 7115. (h) Koot, W.-J.; Hiemstra, H.; Speckamp, W. N. Tetrahedron Lett. 1992, 33, 7969. (i) Kano, S.; Yuasa, Y.; Shibuya, S. Heterocydes 1985, 23, 365. (j) Maryanoff, B. E.; Molinari, A. J.; McComsey, D. F.; Maryanoff, C. A.; Wooden, G. P.; Olofson, R. A. J. Org. Chem. 1983, 48, 5074. See also ref 18a.
80. Miyaura, N.; Suzuki, A. Chem. Rev. 1995, 95, 2457.
81. (a) Heck, R. F. Org. React. 1982, 27, 345.
82. (b) Crisp, G. T. Chem. Soc. Rev. 1998, 27, 427.
83. Farina, V.; Krishnamurthy, V.; Scott, W. J. Org. React. 1997, 50, 1.