Multicomponent reactions with dihydroazines: Efficient synthesis of a diverse set of pyrido-fused tetrahydroquinolines

Journal of Combinatorial Chemistry

Volumn 7, Issue 1, 2005, Pages 33-41

  Carranco, Inés ^a   Díaz, José Luis ^a   Jiménez, Oscar ^a   Vendrell, Marc ^a   Albericio, Fernando ^a   Royo, Miriam ^a   Lavilla, Rodolfo ^a  

^a UNIVERSITY OF BARCELONA   (Spain)

Author keywords

[No Author keywords available]

Indexed keywords

ALDEHYDE DERIVATIVE; ANILINE DERIVATIVE; CARBONYL DERIVATIVE; HETEROCYCLIC COMPOUND; QUINOLINE DERIVATIVE; SOLVENT;

ARTICLE; BIOMIMETICS; CATALYST; COMBINATORIAL LIBRARY; MICROWAVE RADIATION; MOLECULAR INTERACTION; ORGANIC CHEMISTRY; PRESSURE MEASUREMENT; PROCESS DEVELOPMENT; QUANTUM YIELD; REACTION ANALYSIS; REDUCTION; SOLID; SOLVENT EFFECT; SYNTHESIS; THERMODYNAMICS;

ALDEHYDES; ANILINE COMPOUNDS; CATALYSIS; COMBINATORIAL CHEMISTRY TECHNIQUES; HYDROGEN; MOLECULAR STRUCTURE; PYRIDONES; QUINOLINES;

EID: 13544253604     PISSN: 15204766     EISSN: None     Source Type: Journal    
DOI: 10.1021/cc049877a     Document Type: Article

References (103)

1. (a) Wender, P. A.; Handy, S. T.; Wright, S. L. Chem. Ind. 1997, 765.
2. (b) Nicolaou, K. C.; Snyder, S. A. In Classics in Total Synthesis II; Wiley-VCH: Weinheim, Germany, 2003; Chapter 1.
3. (c) de la Torre, M. C.; Sierra, M. A. Angew. Chem., Int. Ed. 2003, 43, 160.
4. (a) Gordon, E. M.; Gallop, M. A.; Patel, D. V. Acc. Chem. Res. 1996, 29, 144.
5. (b) Reader, J. C. Curr. Top. Med. Chem. 2004, 4, 671.
6. (c) Sanchez-Martin R. M.; Mittoo S.; Bradley M. Curr. Top. Med. Chem. 2004, 4, 653.
7. (a) Burke, M. D.; Berger, E. M.; Schreiber, S. L. Science 2003, 302, 613.
8. (b) Spring, D. R. Org. Biomol. Chem. 2003, 1, 3867.
9. (c) Burke, M. D.; Schreiber, S. L. Angew. Chem., Int. Ed. 2004, 43, 46.
10. (a) Wess, G.; Urmann, N.; Sickenberger, B. Angew. Chem., Int. Ed. 2001, 40, 3341.
11. (b) Muegge, I. Chem. - Eur. J. 2002, 8, 1977.
12. (c) Merlot, C.; Domine, D.; Cleva, C.; Church, D. J. Drug Discovery Today 2003, 8, 594.
13. (a) Collins, I. J. Chem. Soc. Perkin Trans. 1 2002, 1921.
14. (b) Gordeev, M. F.; Patel, D. V.; Gordon, E. M. J. Org. Chem. 1996, 61, 924.
15. (c) Lorsbach, B. A.; Bagdanoff, J. T.; Miller, R. B.; Kurth, M. J. J. Org. Chem. 1998, 63, 2244.
16. (d) Munoz, B.; Chen, C.; McDonald, I. A. Biotechnol. Bioeng. 2000, 71, 78.
17. (e) Pelish, H. E.; Westwood, N. J.; Feng, Y.; Kirchhausen, T.; Shair, M. D. J. Am. Chem. Soc. 2001, 123, 6740.
18. (f) Ding, S.; Gray, N. S.; Wu, X.; Ding, Q.; Schultz, P. G. J. Am. Chem. Soc. 2002, 124, 1594.
19. For recent reviews, see: (a) Ugi, I.; Domling, A.; Werner, B. J. Heterocycl. Chem. 2000, 37, 647. (b) Bienaymé, H.; Hulme, C.; Oddon, G.; Schmitt, P. Chem. - Eur. J. 2000, 6, 3321. (c) Dömling, A.; Ugi, I. Angew. Chem., Int. Ed. 2000, 39, 3168. (d) Ugi, I.; Heck, S. Comb. Chem. High Throughput Screening 2001, 4, 1. (e) Ugi, I. Pure Appl. Chem. 2001, 73, 187. (d) Orru, R. V. A.; de Greef, M. Synthesis 2003, 1471. (f) Hulme, C.; Gore, V. Curr. Med. Chem. 2003, 10, 51.
20. For recent reviews, see: (a) Ugi, I.; Domling, A.; Werner, B. J. Heterocycl. Chem. 2000, 37, 647. (b) Bienaymé, H.; Hulme, C.; Oddon, G.; Schmitt, P. Chem. - Eur. J. 2000, 6, 3321. (c) Dom̈ling, A.; Ugi, I. Angew. Chem., Int. Ed. 2000, 39, 3168. (d) Ugi, I.; Heck, S. Comb. Chem. High Throughput Screening 2001, 4, 1. (e) Ugi, I. Pure Appl. Chem. 2001, 73, 187. (d) Orru, R. V. A.; de Greef, M. Synthesis 2003, 1471. (f) Hulme, C.; Gore, V. Curr. Med. Chem. 2003, 10, 51.
21. For recent reviews, see: (a) Ugi, I.; Domling, A.; Werner, B. J. Heterocycl. Chem. 2000, 37, 647. (b) Bienaymé, H.; Hulme, C.; Oddon, G.; Schmitt, P. Chem. - Eur. J. 2000, 6, 3321. (c) Dömling, A.; Ugi, I. Angew. Chem., Int. Ed. 2000, 39, 3168. (d) Ugi, I.; Heck, S. Comb. Chem. High Throughput Screening 2001, 4, 1. (e) Ugi, I. Pure Appl. Chem. 2001, 73, 187. (d) Orru, R. V. A.; de Greef, M. Synthesis 2003, 1471. (f) Hulme, C.; Gore, V. Curr. Med. Chem. 2003, 10, 51.
22. For recent reviews, see: (a) Ugi, I.; Domling, A.; Werner, B. J. Heterocycl. Chem. 2000, 37, 647. (b) Bienaymé, H.; Hulme, C.; Oddon, G.; Schmitt, P. Chem. - Eur. J. 2000, 6, 3321. (c) Dömling, A.; Ugi, I. Angew. Chem., Int. Ed. 2000, 39, 3168. (d) Ugi, I.; Heck, S. Comb. Chem. High Throughput Screening 2001, 4, 1. (e) Ugi, I. Pure Appl. Chem. 2001, 73, 187. (d) Orru, R. V. A.; de Greef, M. Synthesis 2003, 1471. (f) Hulme, C.; Gore, V. Curr. Med. Chem. 2003, 10, 51.
23. For recent reviews, see: (a) Ugi, I.; Domling, A.; Werner, B. J. Heterocycl. Chem. 2000, 37, 647. (b) Bienaymé, H.; Hulme, C.; Oddon, G.; Schmitt, P. Chem. - Eur. J. 2000, 6, 3321. (c) Dom̈ling, A.; Ugi, I. Angew. Chem., Int. Ed. 2000, 39, 3168. (d) Ugi, I.; Heck, S. Comb. Chem. High Throughput Screening 2001, 4, 1. (e) Ugi, I. Pure Appl. Chem. 2001, 73, 187. (d) Orru, R. V. A.; de Greef, M. Synthesis 2003, 1471. (f) Hulme, C.; Gore, V. Curr. Med. Chem. 2003, 10, 51.
24. For recent reviews, see: (a) Ugi, I.; Domling, A.; Werner, B. J. Heterocycl. Chem. 2000, 37, 647. (b) Bienaymé, H.; Hulme, C.; Oddon, G.; Schmitt, P. Chem. - Eur. J. 2000, 6, 3321. (c) Dömling, A.; Ugi, I. Angew. Chem., Int. Ed. 2000, 39, 3168. (d) Ugi, I.; Heck, S. Comb. Chem. High Throughput Screening 2001, 4, 1. (e) Ugi, I. Pure Appl. Chem. 2001, 73, 187. (d) Orru, R. V. A.; de Greef, M. Synthesis 2003, 1471. (f) Hulme, C.; Gore, V. Curr. Med. Chem. 2003, 10, 51.
25. For recent reviews, see: (a) Ugi, I.; Domling, A.; Werner, B. J. Heterocycl. Chem. 2000, 37, 647. (b) Bienaymé, H.; Hulme, C.; Oddon, G.; Schmitt, P. Chem. - Eur. J. 2000, 6, 3321. (c) Dömling, A.; Ugi, I. Angew. Chem., Int. Ed. 2000, 39, 3168. (d) Ugi, I.; Heck, S. Comb. Chem. High Throughput Screening 2001, 4, 1. (e) Ugi, I. Pure Appl. Chem. 2001, 73, 187. (d) Orru, R. V. A.; de Greef, M. Synthesis 2003, 1471. (f) Hulme, C.; Gore, V. Curr. Med. Chem. 2003, 10, 51.
26. (a) Lounasmaa, M.; Tolvanen, A. In Comprehensive Heterocyclic Chemistry II; Katritzky, A. R., Rees, C. W., Scriven, E. F. V., Eds.; Pergamon: Oxford, 1996; Vol. 5, p 135.
27. (b) For a recent review, see: Lavilla, R. J. Chem. Soc., Perkin Trans, 1 2002, 1141.
28. Lavilla, R. Curr. Org. Chem. 2004, 8, 715.
29. (a) Poparov, L. S. Russ. Chem. Rev. 1967, 36, 656.
30. (b) Grieco, P.; Bashas, A. Tetrahedron Lett. 1988, 29, 5855.
31. For a review of tetrahydroquinoline synthesis, see: Katritzky, A. R.; Rachwal, S.; Rachwal, B. Tetrahedron 1996, 52, 15031.
32. For leading references, see: (a) Cabral, J.; Laszlo, P. Tetrahedron Lett. 1989, 30, 7237. (b) Lucchini, V.; Prato, M.; Scorrano, G.; Stivanello, M.; Valle, G. J. Chem. Soc., Perkin Trans. 2 1992, 259. (c) Mellor, J. M.; Merriman, G. D. Tetrahedron 1995, 51, 6115. (d) Kobayashi, S.; Ishitani, H.; Nagayama, S. Synlett 1995, 1195. (e) Makioka, Y.; Shindo, T.; Taniguchi, Y.; Takaki, K.; Fujiwara, Y. Synthesis 1995, 801. (f) Baudelle, R.; Melnyck, P.; Déprez, B.; Tartar, A. Tetrahedron 1998, 54, 4125. (g) Kyselyov, A. S.; Smith, L.; Armstrong, R. W. Tetrahedron 1998, 54, 5089. (h) Babu, G.; Perumal, P. T. Tetrahedron Lett. 1998, 39, 3225. (i) Ma, Y.; Quian, C.; Xie, M.; Sun, J. J. Org. Chem. 1999, 64, 6462. (j) Gadhwal, S.; Sandhu, J. S. J. Chem. Soc, Perkin Trans. 1 2000, 2827. (k) Crousse, B.; Bégué, J.-P.; Bonnet-Delpon, D. J. Org. Chem. 2000, 65, 5009. (l) Sundararajan, G.; Prabagaran, N.; Varghese, B. Org. Lett. 2001, 3, 1973. (m) Sabitha, G.; Venkata, E. R.; Yadav, J. S. Synthesis 2001, 1979. (n) Powell, D. A.; Batey, R. A. Org. Lett. 2002, 4, 2913. (o) Stevenson, P. J.; Nieuwenhuyzen, M.; Osborne, D. Chem. Commun. 2002, 444. (p) Zhang, J.; Li, C.-J. J. Org. Chem. 2002, 67, 3969. (q) Cheng, D.; Zhou, J.; Saiah, E.; Beaton, G. Org. Lett. 2002, 4, 4411. (r) Bailey, P. D.; Smith, P. D.; Morgan, K. M.; Rosair, G. M. Tetrahedron Lett. 2002, 43, 1071. (s) Hoemann, M. Z.; Xie, R. L.; Rossi, R. F.; Meyer, S.; Sidhu, A.; Cuny, G. D.; Hauske, J. R. Bioorg. Med. Chem. Lett. 2002, 12, 129. (t) Magomedov, N. A. Org. Lett. 2003, 5, 2509.
33. For leading references, see: (a) Cabral, J.; Laszlo, P. Tetrahedron Lett. 1989, 30, 7237. (b) Lucchini, V.; Prato, M.; Scorrano, G.; Stivanello, M.; Valle, G. J. Chem. Soc., Perkin Trans. 2 1992, 259. (c) Mellor, J. M.; Merriman, G. D. Tetrahedron 1995, 51, 6115. (d) Kobayashi, S.; Ishitani, H.; Nagayama, S. Synlett 1995, 1195. (e) Makioka, Y.; Shindo, T.; Taniguchi, Y.; Takaki, K.; Fujiwara, Y. Synthesis 1995, 801. (f) Baudelle, R.; Melnyck, P.; Déprez, B.; Tartar, A. Tetrahedron 1998, 54, 4125. (g) Kyselyov, A. S.; Smith, L.; Armstrong, R. W. Tetrahedron 1998, 54, 5089. (h) Babu, G.; Perumal, P. T. Tetrahedron Lett. 1998, 39, 3225. (i) Ma, Y.; Quian, C.; Xie, M.; Sun, J. J. Org. Chem. 1999, 64, 6462. (j) Gadhwal, S.; Sandhu, J. S. J. Chem. Soc, Perkin Trans. 1 2000, 2827. (k) Crousse, B.; Bégué, J.-P.; Bonnet-Delpon, D. J. Org. Chem. 2000, 65, 5009. (l) Sundararajan, G.; Prabagaran, N.; Varghese, B. Org. Lett. 2001, 3, 1973. (m) Sabitha, G.; Venkata, E. R.; Yadav, J. S. Synthesis 2001, 1979. (n) Powell, D. A.; Batey, R. A. Org. Lett. 2002, 4, 2913. (o) Stevenson, P. J.; Nieuwenhuyzen, M.; Osborne, D. Chem. Commun. 2002, 444. (p) Zhang, J.; Li, C.-J. J. Org. Chem. 2002, 67, 3969. (q) Cheng, D.; Zhou, J.; Saiah, E.; Beaton, G. Org. Lett. 2002, 4, 4411. (r) Bailey, P. D.; Smith, P. D.; Morgan, K. M.; Rosair, G. M. Tetrahedron Lett. 2002, 43, 1071. (s) Hoemann, M. Z.; Xie, R. L.; Rossi, R. F.; Meyer, S.; Sidhu, A.; Cuny, G. D.; Hauske, J. R. Bioorg. Med. Chem. Lett. 2002, 12, 129. (t) Magomedov, N. A. Org. Lett. 2003, 5, 2509.
34. For leading references, see: (a) Cabral, J.; Laszlo, P. Tetrahedron Lett. 1989, 30, 7237. (b) Lucchini, V.; Prato, M.; Scorrano, G.; Stivanello, M.; Valle, G. J. Chem. Soc., Perkin Trans. 2 1992, 259. (c) Mellor, J. M.; Merriman, G. D. Tetrahedron 1995, 51, 6115. (d) Kobayashi, S.; Ishitani, H.; Nagayama, S. Synlett 1995, 1195. (e) Makioka, Y.; Shindo, T.; Taniguchi, Y.; Takaki, K.; Fujiwara, Y. Synthesis 1995, 801. (f) Baudelle, R.; Melnyck, P.; Déprez, B.; Tartar, A. Tetrahedron 1998, 54, 4125. (g) Kyselyov, A. S.; Smith, L.; Armstrong, R. W. Tetrahedron 1998, 54, 5089. (h) Babu, G.; Perumal, P. T. Tetrahedron Lett. 1998, 39, 3225. (i) Ma, Y.; Quian, C.; Xie, M.; Sun, J. J. Org. Chem. 1999, 64, 6462. (j) Gadhwal, S.; Sandhu, J. S. J. Chem. Soc, Perkin Trans. 1 2000, 2827. (k) Crousse, B.; Bégué, J.-P.; Bonnet-Delpon, D. J. Org. Chem. 2000, 65, 5009. (l) Sundararajan, G.; Prabagaran, N.; Varghese, B. Org. Lett. 2001, 3, 1973. (m) Sabitha, G.; Venkata, E. R.; Yadav, J. S. Synthesis 2001, 1979. (n) Powell, D. A.; Batey, R. A. Org. Lett. 2002, 4, 2913. (o) Stevenson, P. J.; Nieuwenhuyzen, M.; Osborne, D. Chem. Commun. 2002, 444. (p) Zhang, J.; Li, C.-J. J. Org. Chem. 2002, 67, 3969. (q) Cheng, D.; Zhou, J.; Saiah, E.; Beaton, G. Org. Lett. 2002, 4, 4411. (r) Bailey, P. D.; Smith, P. D.; Morgan, K. M.; Rosair, G. M. Tetrahedron Lett. 2002, 43, 1071. (s) Hoemann, M. Z.; Xie, R. L.; Rossi, R. F.; Meyer, S.; Sidhu, A.; Cuny, G. D.; Hauske, J. R. Bioorg. Med. Chem. Lett. 2002, 12, 129. (t) Magomedov, N. A. Org. Lett. 2003, 5, 2509.
35. For leading references, see: (a) Cabral, J.; Laszlo, P. Tetrahedron Lett. 1989, 30, 7237. (b) Lucchini, V.; Prato, M.; Scorrano, G.; Stivanello, M.; Valle, G. J. Chem. Soc., Perkin Trans. 2 1992, 259. (c) Mellor, J. M.; Merriman, G. D. Tetrahedron 1995, 51, 6115. (d) Kobayashi, S.; Ishitani, H.; Nagayama, S. Synlett 1995, 1195. (e) Makioka, Y.; Shindo, T.; Taniguchi, Y.; Takaki, K.; Fujiwara, Y. Synthesis 1995, 801. (f) Baudelle, R.; Melnyck, P.; Déprez, B.; Tartar, A. Tetrahedron 1998, 54, 4125. (g) Kyselyov, A. S.; Smith, L.; Armstrong, R. W. Tetrahedron 1998, 54, 5089. (h) Babu, G.; Perumal, P. T. Tetrahedron Lett. 1998, 39, 3225. (i) Ma, Y.; Quian, C.; Xie, M.; Sun, J. J. Org. Chem. 1999, 64, 6462. (j) Gadhwal, S.; Sandhu, J. S. J. Chem. Soc, Perkin Trans. 1 2000, 2827. (k) Crousse, B.; Bégué, J.-P.; Bonnet-Delpon, D. J. Org. Chem. 2000, 65, 5009. (l) Sundararajan, G.; Prabagaran, N.; Varghese, B. Org. Lett. 2001, 3, 1973. (m) Sabitha, G.; Venkata, E. R.; Yadav, J. S. Synthesis 2001, 1979. (n) Powell, D. A.; Batey, R. A. Org. Lett. 2002, 4, 2913. (o) Stevenson, P. J.; Nieuwenhuyzen, M.; Osborne, D. Chem. Commun. 2002, 444. (p) Zhang, J.; Li, C.-J. J. Org. Chem. 2002, 67, 3969. (q) Cheng, D.; Zhou, J.; Saiah, E.; Beaton, G. Org. Lett. 2002, 4, 4411. (r) Bailey, P. D.; Smith, P. D.; Morgan, K. M.; Rosair, G. M. Tetrahedron Lett. 2002, 43, 1071. (s) Hoemann, M. Z.; Xie, R. L.; Rossi, R. F.; Meyer, S.; Sidhu, A.; Cuny, G. D.; Hauske, J. R. Bioorg. Med. Chem. Lett. 2002, 12, 129. (t) Magomedov, N. A. Org. Lett. 2003, 5, 2509.
36. For leading references, see: (a) Cabral, J.; Laszlo, P. Tetrahedron Lett. 1989, 30, 7237. (b) Lucchini, V.; Prato, M.; Scorrano, G.; Stivanello, M.; Valle, G. J. Chem. Soc., Perkin Trans. 2 1992, 259. (c) Mellor, J. M.; Merriman, G. D. Tetrahedron 1995, 51, 6115. (d) Kobayashi, S.; Ishitani, H.; Nagayama, S. Synlett 1995, 1195. (e) Makioka, Y.; Shindo, T.; Taniguchi, Y.; Takaki, K.; Fujiwara, Y. Synthesis 1995, 801. (f) Baudelle, R.; Melnyck, P.; Déprez, B.; Tartar, A. Tetrahedron 1998, 54, 4125. (g) Kyselyov, A. S.; Smith, L.; Armstrong, R. W. Tetrahedron 1998, 54, 5089. (h) Babu, G.; Perumal, P. T. Tetrahedron Lett. 1998, 39, 3225. (i) Ma, Y.; Quian, C.; Xie, M.; Sun, J. J. Org. Chem. 1999, 64, 6462. (j) Gadhwal, S.; Sandhu, J. S. J. Chem. Soc, Perkin Trans. 1 2000, 2827. (k) Crousse, B.; Bégué, J.-P.; Bonnet-Delpon, D. J. Org. Chem. 2000, 65, 5009. (l) Sundararajan, G.; Prabagaran, N.; Varghese, B. Org. Lett. 2001, 3, 1973. (m) Sabitha, G.; Venkata, E. R.; Yadav, J. S. Synthesis 2001, 1979. (n) Powell, D. A.; Batey, R. A. Org. Lett. 2002, 4, 2913. (o) Stevenson, P. J.; Nieuwenhuyzen, M.; Osborne, D. Chem. Commun. 2002, 444. (p) Zhang, J.; Li, C.-J. J. Org. Chem. 2002, 67, 3969. (q) Cheng, D.; Zhou, J.; Saiah, E.; Beaton, G. Org. Lett. 2002, 4, 4411. (r) Bailey, P. D.; Smith, P. D.; Morgan, K. M.; Rosair, G. M. Tetrahedron Lett. 2002, 43, 1071. (s) Hoemann, M. Z.; Xie, R. L.; Rossi, R. F.; Meyer, S.; Sidhu, A.; Cuny, G. D.; Hauske, J. R. Bioorg. Med. Chem. Lett. 2002, 12, 129. (t) Magomedov, N. A. Org. Lett. 2003, 5, 2509.
37. For leading references, see: (a) Cabral, J.; Laszlo, P. Tetrahedron Lett. 1989, 30, 7237. (b) Lucchini, V.; Prato, M.; Scorrano, G.; Stivanello, M.; Valle, G. J. Chem. Soc., Perkin Trans. 2 1992, 259. (c) Mellor, J. M.; Merriman, G. D. Tetrahedron 1995, 51, 6115. (d) Kobayashi, S.; Ishitani, H.; Nagayama, S. Synlett 1995, 1195. (e) Makioka, Y.; Shindo, T.; Taniguchi, Y.; Takaki, K.; Fujiwara, Y. Synthesis 1995, 801. (f) Baudelle, R.; Melnyck, P.; Déprez, B.; Tartar, A. Tetrahedron 1998, 54, 4125. (g) Kyselyov, A. S.; Smith, L.; Armstrong, R. W. Tetrahedron 1998, 54, 5089. (h) Babu, G.; Perumal, P. T. Tetrahedron Lett. 1998, 39, 3225. (i) Ma, Y.; Quian, C.; Xie, M.; Sun, J. J. Org. Chem. 1999, 64, 6462. (j) Gadhwal, S.; Sandhu, J. S. J. Chem. Soc, Perkin Trans. 1 2000, 2827. (k) Crousse, B.; Bégué, J.-P.; Bonnet-Delpon, D. J. Org. Chem. 2000, 65, 5009. (l) Sundararajan, G.; Prabagaran, N.; Varghese, B. Org. Lett. 2001, 3, 1973. (m) Sabitha, G.; Venkata, E. R.; Yadav, J. S. Synthesis 2001, 1979. (n) Powell, D. A.; Batey, R. A. Org. Lett. 2002, 4, 2913. (o) Stevenson, P. J.; Nieuwenhuyzen, M.; Osborne, D. Chem. Commun. 2002, 444. (p) Zhang, J.; Li, C.-J. J. Org. Chem. 2002, 67, 3969. (q) Cheng, D.; Zhou, J.; Saiah, E.; Beaton, G. Org. Lett. 2002, 4, 4411. (r) Bailey, P. D.; Smith, P. D.; Morgan, K. M.; Rosair, G. M. Tetrahedron Lett. 2002, 43, 1071. (s) Hoemann, M. Z.; Xie, R. L.; Rossi, R. F.; Meyer, S.; Sidhu, A.; Cuny, G. D.; Hauske, J. R. Bioorg. Med. Chem. Lett. 2002, 12, 129. (t) Magomedov, N. A. Org. Lett. 2003, 5, 2509.
38. For leading references, see: (a) Cabral, J.; Laszlo, P. Tetrahedron Lett. 1989, 30, 7237. (b) Lucchini, V.; Prato, M.; Scorrano, G.; Stivanello, M.; Valle, G. J. Chem. Soc., Perkin Trans. 2 1992, 259. (c) Mellor, J. M.; Merriman, G. D. Tetrahedron 1995, 51, 6115. (d) Kobayashi, S.; Ishitani, H.; Nagayama, S. Synlett 1995, 1195. (e) Makioka, Y.; Shindo, T.; Taniguchi, Y.; Takaki, K.; Fujiwara, Y. Synthesis 1995, 801. (f) Baudelle, R.; Melnyck, P.; Déprez, B.; Tartar, A. Tetrahedron 1998, 54, 4125. (g) Kyselyov, A. S.; Smith, L.; Armstrong, R. W. Tetrahedron 1998, 54, 5089. (h) Babu, G.; Perumal, P. T. Tetrahedron Lett. 1998, 39, 3225. (i) Ma, Y.; Quian, C.; Xie, M.; Sun, J. J. Org. Chem. 1999, 64, 6462. (j) Gadhwal, S.; Sandhu, J. S. J. Chem. Soc, Perkin Trans. 1 2000, 2827. (k) Crousse, B.; Bégué, J.-P.; Bonnet-Delpon, D. J. Org. Chem. 2000, 65, 5009. (l) Sundararajan, G.; Prabagaran, N.; Varghese, B. Org. Lett. 2001, 3, 1973. (m) Sabitha, G.; Venkata, E. R.; Yadav, J. S. Synthesis 2001, 1979. (n) Powell, D. A.; Batey, R. A. Org. Lett. 2002, 4, 2913. (o) Stevenson, P. J.; Nieuwenhuyzen, M.; Osborne, D. Chem. Commun. 2002, 444. (p) Zhang, J.; Li, C.-J. J. Org. Chem. 2002, 67, 3969. (q) Cheng, D.; Zhou, J.; Saiah, E.; Beaton, G. Org. Lett. 2002, 4, 4411. (r) Bailey, P. D.; Smith, P. D.; Morgan, K. M.; Rosair, G. M. Tetrahedron Lett. 2002, 43, 1071. (s) Hoemann, M. Z.; Xie, R. L.; Rossi, R. F.; Meyer, S.; Sidhu, A.; Cuny, G. D.; Hauske, J. R. Bioorg. Med. Chem. Lett. 2002, 12, 129. (t) Magomedov, N. A. Org. Lett. 2003, 5, 2509.
39. For leading references, see: (a) Cabral, J.; Laszlo, P. Tetrahedron Lett. 1989, 30, 7237. (b) Lucchini, V.; Prato, M.; Scorrano, G.; Stivanello, M.; Valle, G. J. Chem. Soc., Perkin Trans. 2 1992, 259. (c) Mellor, J. M.; Merriman, G. D. Tetrahedron 1995, 51, 6115. (d) Kobayashi, S.; Ishitani, H.; Nagayama, S. Synlett 1995, 1195. (e) Makioka, Y.; Shindo, T.; Taniguchi, Y.; Takaki, K.; Fujiwara, Y. Synthesis 1995, 801. (f) Baudelle, R.; Melnyck, P.; Déprez, B.; Tartar, A. Tetrahedron 1998, 54, 4125. (g) Kyselyov, A. S.; Smith, L.; Armstrong, R. W. Tetrahedron 1998, 54, 5089. (h) Babu, G.; Perumal, P. T. Tetrahedron Lett. 1998, 39, 3225. (i) Ma, Y.; Quian, C.; Xie, M.; Sun, J. J. Org. Chem. 1999, 64, 6462. (j) Gadhwal, S.; Sandhu, J. S. J. Chem. Soc, Perkin Trans. 1 2000, 2827. (k) Crousse, B.; Bégué, J.-P.; Bonnet-Delpon, D. J. Org. Chem. 2000, 65, 5009. (l) Sundararajan, G.; Prabagaran, N.; Varghese, B. Org. Lett. 2001, 3, 1973. (m) Sabitha, G.; Venkata, E. R.; Yadav, J. S. Synthesis 2001, 1979. (n) Powell, D. A.; Batey, R. A. Org. Lett. 2002, 4, 2913. (o) Stevenson, P. J.; Nieuwenhuyzen, M.; Osborne, D. Chem. Commun. 2002, 444. (p) Zhang, J.; Li, C.-J. J. Org. Chem. 2002, 67, 3969. (q) Cheng, D.; Zhou, J.; Saiah, E.; Beaton, G. Org. Lett. 2002, 4, 4411. (r) Bailey, P. D.; Smith, P. D.; Morgan, K. M.; Rosair, G. M. Tetrahedron Lett. 2002, 43, 1071. (s) Hoemann, M. Z.; Xie, R. L.; Rossi, R. F.; Meyer, S.; Sidhu, A.; Cuny, G. D.; Hauske, J. R. Bioorg. Med. Chem. Lett. 2002, 12, 129. (t) Magomedov, N. A. Org. Lett. 2003, 5, 2509.
40. For leading references, see: (a) Cabral, J.; Laszlo, P. Tetrahedron Lett. 1989, 30, 7237. (b) Lucchini, V.; Prato, M.; Scorrano, G.; Stivanello, M.; Valle, G. J. Chem. Soc., Perkin Trans. 2 1992, 259. (c) Mellor, J. M.; Merriman, G. D. Tetrahedron 1995, 51, 6115. (d) Kobayashi, S.; Ishitani, H.; Nagayama, S. Synlett 1995, 1195. (e) Makioka, Y.; Shindo, T.; Taniguchi, Y.; Takaki, K.; Fujiwara, Y. Synthesis 1995, 801. (f) Baudelle, R.; Melnyck, P.; Déprez, B.; Tartar, A. Tetrahedron 1998, 54, 4125. (g) Kyselyov, A. S.; Smith, L.; Armstrong, R. W. Tetrahedron 1998, 54, 5089. (h) Babu, G.; Perumal, P. T. Tetrahedron Lett. 1998, 39, 3225. (i) Ma, Y.; Quian, C.; Xie, M.; Sun, J. J. Org. Chem. 1999, 64, 6462. (j) Gadhwal, S.; Sandhu, J. S. J. Chem. Soc, Perkin Trans. 1 2000, 2827. (k) Crousse, B.; Bégué, J.-P.; Bonnet-Delpon, D. J. Org. Chem. 2000, 65, 5009. (l) Sundararajan, G.; Prabagaran, N.; Varghese, B. Org. Lett. 2001, 3, 1973. (m) Sabitha, G.; Venkata, E. R.; Yadav, J. S. Synthesis 2001, 1979. (n) Powell, D. A.; Batey, R. A. Org. Lett. 2002, 4, 2913. (o) Stevenson, P. J.; Nieuwenhuyzen, M.; Osborne, D. Chem. Commun. 2002, 444. (p) Zhang, J.; Li, C.-J. J. Org. Chem. 2002, 67, 3969. (q) Cheng, D.; Zhou, J.; Saiah, E.; Beaton, G. Org. Lett. 2002, 4, 4411. (r) Bailey, P. D.; Smith, P. D.; Morgan, K. M.; Rosair, G. M. Tetrahedron Lett. 2002, 43, 1071. (s) Hoemann, M. Z.; Xie, R. L.; Rossi, R. F.; Meyer, S.; Sidhu, A.; Cuny, G. D.; Hauske, J. R. Bioorg. Med. Chem. Lett. 2002, 12, 129. (t) Magomedov, N. A. Org. Lett. 2003, 5, 2509.
41. For leading references, see: (a) Cabral, J.; Laszlo, P. Tetrahedron Lett. 1989, 30, 7237. (b) Lucchini, V.; Prato, M.; Scorrano, G.; Stivanello, M.; Valle, G. J. Chem. Soc., Perkin Trans. 2 1992, 259. (c) Mellor, J. M.; Merriman, G. D. Tetrahedron 1995, 51, 6115. (d) Kobayashi, S.; Ishitani, H.; Nagayama, S. Synlett 1995, 1195. (e) Makioka, Y.; Shindo, T.; Taniguchi, Y.; Takaki, K.; Fujiwara, Y. Synthesis 1995, 801. (f) Baudelle, R.; Melnyck, P.; Déprez, B.; Tartar, A. Tetrahedron 1998, 54, 4125. (g) Kyselyov, A. S.; Smith, L.; Armstrong, R. W. Tetrahedron 1998, 54, 5089. (h) Babu, G.; Perumal, P. T. Tetrahedron Lett. 1998, 39, 3225. (i) Ma, Y.; Quian, C.; Xie, M.; Sun, J. J. Org. Chem. 1999, 64, 6462. (j) Gadhwal, S.; Sandhu, J. S. J. Chem. Soc, Perkin Trans. 1 2000, 2827. (k) Crousse, B.; Bégué, J.-P.; Bonnet-Delpon, D. J. Org. Chem. 2000, 65, 5009. (l) Sundararajan, G.; Prabagaran, N.; Varghese, B. Org. Lett. 2001, 3, 1973. (m) Sabitha, G.; Venkata, E. R.; Yadav, J. S. Synthesis 2001, 1979. (n) Powell, D. A.; Batey, R. A. Org. Lett. 2002, 4, 2913. (o) Stevenson, P. J.; Nieuwenhuyzen, M.; Osborne, D. Chem. Commun. 2002, 444. (p) Zhang, J.; Li, C.-J. J. Org. Chem. 2002, 67, 3969. (q) Cheng, D.; Zhou, J.; Saiah, E.; Beaton, G. Org. Lett. 2002, 4, 4411. (r) Bailey, P. D.; Smith, P. D.; Morgan, K. M.; Rosair, G. M. Tetrahedron Lett. 2002, 43, 1071. (s) Hoemann, M. Z.; Xie, R. L.; Rossi, R. F.; Meyer, S.; Sidhu, A.; Cuny, G. D.; Hauske, J. R. Bioorg. Med. Chem. Lett. 2002, 12, 129. (t) Magomedov, N. A. Org. Lett. 2003, 5, 2509.
42. For leading references, see: (a) Cabral, J.; Laszlo, P. Tetrahedron Lett. 1989, 30, 7237. (b) Lucchini, V.; Prato, M.; Scorrano, G.; Stivanello, M.; Valle, G. J. Chem. Soc., Perkin Trans. 2 1992, 259. (c) Mellor, J. M.; Merriman, G. D. Tetrahedron 1995, 51, 6115. (d) Kobayashi, S.; Ishitani, H.; Nagayama, S. Synlett 1995, 1195. (e) Makioka, Y.; Shindo, T.; Taniguchi, Y.; Takaki, K.; Fujiwara, Y. Synthesis 1995, 801. (f) Baudelle, R.; Melnyck, P.; Déprez, B.; Tartar, A. Tetrahedron 1998, 54, 4125. (g) Kyselyov, A. S.; Smith, L.; Armstrong, R. W. Tetrahedron 1998, 54, 5089. (h) Babu, G.; Perumal, P. T. Tetrahedron Lett. 1998, 39, 3225. (i) Ma, Y.; Quian, C.; Xie, M.; Sun, J. J. Org. Chem. 1999, 64, 6462. (j) Gadhwal, S.; Sandhu, J. S. J. Chem. Soc, Perkin Trans. 1 2000, 2827. (k) Crousse, B.; Bégué, J.-P.; Bonnet-Delpon, D. J. Org. Chem. 2000, 65, 5009. (l) Sundararajan, G.; Prabagaran, N.; Varghese, B. Org. Lett. 2001, 3, 1973. (m) Sabitha, G.; Venkata, E. R.; Yadav, J. S. Synthesis 2001, 1979. (n) Powell, D. A.; Batey, R. A. Org. Lett. 2002, 4, 2913. (o) Stevenson, P. J.; Nieuwenhuyzen, M.; Osborne, D. Chem. Commun. 2002, 444. (p) Zhang, J.; Li, C.-J. J. Org. Chem. 2002, 67, 3969. (q) Cheng, D.; Zhou, J.; Saiah, E.; Beaton, G. Org. Lett. 2002, 4, 4411. (r) Bailey, P. D.; Smith, P. D.; Morgan, K. M.; Rosair, G. M. Tetrahedron Lett. 2002, 43, 1071. (s) Hoemann, M. Z.; Xie, R. L.; Rossi, R. F.; Meyer, S.; Sidhu, A.; Cuny, G. D.; Hauske, J. R. Bioorg. Med. Chem. Lett. 2002, 12, 129. (t) Magomedov, N. A. Org. Lett. 2003, 5, 2509.
43. For leading references, see: (a) Cabral, J.; Laszlo, P. Tetrahedron Lett. 1989, 30, 7237. (b) Lucchini, V.; Prato, M.; Scorrano, G.; Stivanello, M.; Valle, G. J. Chem. Soc., Perkin Trans. 2 1992, 259. (c) Mellor, J. M.; Merriman, G. D. Tetrahedron 1995, 51, 6115. (d) Kobayashi, S.; Ishitani, H.; Nagayama, S. Synlett 1995, 1195. (e) Makioka, Y.; Shindo, T.; Taniguchi, Y.; Takaki, K.; Fujiwara, Y. Synthesis 1995, 801. (f) Baudelle, R.; Melnyck, P.; Déprez, B.; Tartar, A. Tetrahedron 1998, 54, 4125. (g) Kyselyov, A. S.; Smith, L.; Armstrong, R. W. Tetrahedron 1998, 54, 5089. (h) Babu, G.; Perumal, P. T. Tetrahedron Lett. 1998, 39, 3225. (i) Ma, Y.; Quian, C.; Xie, M.; Sun, J. J. Org. Chem. 1999, 64, 6462. (j) Gadhwal, S.; Sandhu, J. S. J. Chem. Soc, Perkin Trans. 1 2000, 2827. (k) Crousse, B.; Bégué, J.-P.; Bonnet-Delpon, D. J. Org. Chem. 2000, 65, 5009. (l) Sundararajan, G.; Prabagaran, N.; Varghese, B. Org. Lett. 2001, 3, 1973. (m) Sabitha, G.; Venkata, E. R.; Yadav, J. S. Synthesis 2001, 1979. (n) Powell, D. A.; Batey, R. A. Org. Lett. 2002, 4, 2913. (o) Stevenson, P. J.; Nieuwenhuyzen, M.; Osborne, D. Chem. Commun. 2002, 444. (p) Zhang, J.; Li, C.-J. J. Org. Chem. 2002, 67, 3969. (q) Cheng, D.; Zhou, J.; Saiah, E.; Beaton, G. Org. Lett. 2002, 4, 4411. (r) Bailey, P. D.; Smith, P. D.; Morgan, K. M.; Rosair, G. M. Tetrahedron Lett. 2002, 43, 1071. (s) Hoemann, M. Z.; Xie, R. L.; Rossi, R. F.; Meyer, S.; Sidhu, A.; Cuny, G. D.; Hauske, J. R. Bioorg. Med. Chem. Lett. 2002, 12, 129. (t) Magomedov, N. A. Org. Lett. 2003, 5, 2509.
44. For leading references, see: (a) Cabral, J.; Laszlo, P. Tetrahedron Lett. 1989, 30, 7237. (b) Lucchini, V.; Prato, M.; Scorrano, G.; Stivanello, M.; Valle, G. J. Chem. Soc., Perkin Trans. 2 1992, 259. (c) Mellor, J. M.; Merriman, G. D. Tetrahedron 1995, 51, 6115. (d) Kobayashi, S.; Ishitani, H.; Nagayama, S. Synlett 1995, 1195. (e) Makioka, Y.; Shindo, T.; Taniguchi, Y.; Takaki, K.; Fujiwara, Y. Synthesis 1995, 801. (f) Baudelle, R.; Melnyck, P.; Déprez, B.; Tartar, A. Tetrahedron 1998, 54, 4125. (g) Kyselyov, A. S.; Smith, L.; Armstrong, R. W. Tetrahedron 1998, 54, 5089. (h) Babu, G.; Perumal, P. T. Tetrahedron Lett. 1998, 39, 3225. (i) Ma, Y.; Quian, C.; Xie, M.; Sun, J. J. Org. Chem. 1999, 64, 6462. (j) Gadhwal, S.; Sandhu, J. S. J. Chem. Soc, Perkin Trans. 1 2000, 2827. (k) Crousse, B.; Bégué, J.-P.; Bonnet-Delpon, D. J. Org. Chem. 2000, 65, 5009. (l) Sundararajan, G.; Prabagaran, N.; Varghese, B. Org. Lett. 2001, 3, 1973. (m) Sabitha, G.; Venkata, E. R.; Yadav, J. S. Synthesis 2001, 1979. (n) Powell, D. A.; Batey, R. A. Org. Lett. 2002, 4, 2913. (o) Stevenson, P. J.; Nieuwenhuyzen, M.; Osborne, D. Chem. Commun. 2002, 444. (p) Zhang, J.; Li, C.-J. J. Org. Chem. 2002, 67, 3969. (q) Cheng, D.; Zhou, J.; Saiah, E.; Beaton, G. Org. Lett. 2002, 4, 4411. (r) Bailey, P. D.; Smith, P. D.; Morgan, K. M.; Rosair, G. M. Tetrahedron Lett. 2002, 43, 1071. (s) Hoemann, M. Z.; Xie, R. L.; Rossi, R. F.; Meyer, S.; Sidhu, A.; Cuny, G. D.; Hauske, J. R. Bioorg. Med. Chem. Lett. 2002, 12, 129. (t) Magomedov, N. A. Org. Lett. 2003, 5, 2509.
45. For leading references, see: (a) Cabral, J.; Laszlo, P. Tetrahedron Lett. 1989, 30, 7237. (b) Lucchini, V.; Prato, M.; Scorrano, G.; Stivanello, M.; Valle, G. J. Chem. Soc., Perkin Trans. 2 1992, 259. (c) Mellor, J. M.; Merriman, G. D. Tetrahedron 1995, 51, 6115. (d) Kobayashi, S.; Ishitani, H.; Nagayama, S. Synlett 1995, 1195. (e) Makioka, Y.; Shindo, T.; Taniguchi, Y.; Takaki, K.; Fujiwara, Y. Synthesis 1995, 801. (f) Baudelle, R.; Melnyck, P.; Déprez, B.; Tartar, A. Tetrahedron 1998, 54, 4125. (g) Kyselyov, A. S.; Smith, L.; Armstrong, R. W. Tetrahedron 1998, 54, 5089. (h) Babu, G.; Perumal, P. T. Tetrahedron Lett. 1998, 39, 3225. (i) Ma, Y.; Quian, C.; Xie, M.; Sun, J. J. Org. Chem. 1999, 64, 6462. (j) Gadhwal, S.; Sandhu, J. S. J. Chem. Soc, Perkin Trans. 1 2000, 2827. (k) Crousse, B.; Bégué, J.-P.; Bonnet-Delpon, D. J. Org. Chem. 2000, 65, 5009. (l) Sundararajan, G.; Prabagaran, N.; Varghese, B. Org. Lett. 2001, 3, 1973. (m) Sabitha, G.; Venkata, E. R.; Yadav, J. S. Synthesis 2001, 1979. (n) Powell, D. A.; Batey, R. A. Org. Lett. 2002, 4, 2913. (o) Stevenson, P. J.; Nieuwenhuyzen, M.; Osborne, D. Chem. Commun. 2002, 444. (p) Zhang, J.; Li, C.-J. J. Org. Chem. 2002, 67, 3969. (q) Cheng, D.; Zhou, J.; Saiah, E.; Beaton, G. Org. Lett. 2002, 4, 4411. (r) Bailey, P. D.; Smith, P. D.; Morgan, K. M.; Rosair, G. M. Tetrahedron Lett. 2002, 43, 1071. (s) Hoemann, M. Z.; Xie, R. L.; Rossi, R. F.; Meyer, S.; Sidhu, A.; Cuny, G. D.; Hauske, J. R. Bioorg. Med. Chem. Lett. 2002, 12, 129. (t) Magomedov, N. A. Org. Lett. 2003, 5, 2509.
46. For leading references, see: (a) Cabral, J.; Laszlo, P. Tetrahedron Lett. 1989, 30, 7237. (b) Lucchini, V.; Prato, M.; Scorrano, G.; Stivanello, M.; Valle, G. J. Chem. Soc., Perkin Trans. 2 1992, 259. (c) Mellor, J. M.; Merriman, G. D. Tetrahedron 1995, 51, 6115. (d) Kobayashi, S.; Ishitani, H.; Nagayama, S. Synlett 1995, 1195. (e) Makioka, Y.; Shindo, T.; Taniguchi, Y.; Takaki, K.; Fujiwara, Y. Synthesis 1995, 801. (f) Baudelle, R.; Melnyck, P.; Déprez, B.; Tartar, A. Tetrahedron 1998, 54, 4125. (g) Kyselyov, A. S.; Smith, L.; Armstrong, R. W. Tetrahedron 1998, 54, 5089. (h) Babu, G.; Perumal, P. T. Tetrahedron Lett. 1998, 39, 3225. (i) Ma, Y.; Quian, C.; Xie, M.; Sun, J. J. Org. Chem. 1999, 64, 6462. (j) Gadhwal, S.; Sandhu, J. S. J. Chem. Soc, Perkin Trans. 1 2000, 2827. (k) Crousse, B.; Bégué, J.-P.; Bonnet-Delpon, D. J. Org. Chem. 2000, 65, 5009. (l) Sundararajan, G.; Prabagaran, N.; Varghese, B. Org. Lett. 2001, 3, 1973. (m) Sabitha, G.; Venkata, E. R.; Yadav, J. S. Synthesis 2001, 1979. (n) Powell, D. A.; Batey, R. A. Org. Lett. 2002, 4, 2913. (o) Stevenson, P. J.; Nieuwenhuyzen, M.; Osborne, D. Chem. Commun. 2002, 444. (p) Zhang, J.; Li, C.-J. J. Org. Chem. 2002, 67, 3969. (q) Cheng, D.; Zhou, J.; Saiah, E.; Beaton, G. Org. Lett. 2002, 4, 4411. (r) Bailey, P. D.; Smith, P. D.; Morgan, K. M.; Rosair, G. M. Tetrahedron Lett. 2002, 43, 1071. (s) Hoemann, M. Z.; Xie, R. L.; Rossi, R. F.; Meyer, S.; Sidhu, A.; Cuny, G. D.; Hauske, J. R. Bioorg. Med. Chem. Lett. 2002, 12, 129. (t) Magomedov, N. A. Org. Lett. 2003, 5, 2509.
47. For leading references, see: (a) Cabral, J.; Laszlo, P. Tetrahedron Lett. 1989, 30, 7237. (b) Lucchini, V.; Prato, M.; Scorrano, G.; Stivanello, M.; Valle, G. J. Chem. Soc., Perkin Trans. 2 1992, 259. (c) Mellor, J. M.; Merriman, G. D. Tetrahedron 1995, 51, 6115. (d) Kobayashi, S.; Ishitani, H.; Nagayama, S. Synlett 1995, 1195. (e) Makioka, Y.; Shindo, T.; Taniguchi, Y.; Takaki, K.; Fujiwara, Y. Synthesis 1995, 801. (f) Baudelle, R.; Melnyck, P.; Déprez, B.; Tartar, A. Tetrahedron 1998, 54, 4125. (g) Kyselyov, A. S.; Smith, L.; Armstrong, R. W. Tetrahedron 1998, 54, 5089. (h) Babu, G.; Perumal, P. T. Tetrahedron Lett. 1998, 39, 3225. (i) Ma, Y.; Quian, C.; Xie, M.; Sun, J. J. Org. Chem. 1999, 64, 6462. (j) Gadhwal, S.; Sandhu, J. S. J. Chem. Soc, Perkin Trans. 1 2000, 2827. (k) Crousse, B.; Bégué, J.-P.; Bonnet-Delpon, D. J. Org. Chem. 2000, 65, 5009. (l) Sundararajan, G.; Prabagaran, N.; Varghese, B. Org. Lett. 2001, 3, 1973. (m) Sabitha, G.; Venkata, E. R.; Yadav, J. S. Synthesis 2001, 1979. (n) Powell, D. A.; Batey, R. A. Org. Lett. 2002, 4, 2913. (o) Stevenson, P. J.; Nieuwenhuyzen, M.; Osborne, D. Chem. Commun. 2002, 444. (p) Zhang, J.; Li, C.-J. J. Org. Chem. 2002, 67, 3969. (q) Cheng, D.; Zhou, J.; Saiah, E.; Beaton, G. Org. Lett. 2002, 4, 4411. (r) Bailey, P. D.; Smith, P. D.; Morgan, K. M.; Rosair, G. M. Tetrahedron Lett. 2002, 43, 1071. (s) Hoemann, M. Z.; Xie, R. L.; Rossi, R. F.; Meyer, S.; Sidhu, A.; Cuny, G. D.; Hauske, J. R. Bioorg. Med. Chem. Lett. 2002, 12, 129. (t) Magomedov, N. A. Org. Lett. 2003, 5, 2509.
48. For leading references, see: (a) Cabral, J.; Laszlo, P. Tetrahedron Lett. 1989, 30, 7237. (b) Lucchini, V.; Prato, M.; Scorrano, G.; Stivanello, M.; Valle, G. J. Chem. Soc., Perkin Trans. 2 1992, 259. (c) Mellor, J. M.; Merriman, G. D. Tetrahedron 1995, 51, 6115. (d) Kobayashi, S.; Ishitani, H.; Nagayama, S. Synlett 1995, 1195. (e) Makioka, Y.; Shindo, T.; Taniguchi, Y.; Takaki, K.; Fujiwara, Y. Synthesis 1995, 801. (f) Baudelle, R.; Melnyck, P.; Déprez, B.; Tartar, A. Tetrahedron 1998, 54, 4125. (g) Kyselyov, A. S.; Smith, L.; Armstrong, R. W. Tetrahedron 1998, 54, 5089. (h) Babu, G.; Perumal, P. T. Tetrahedron Lett. 1998, 39, 3225. (i) Ma, Y.; Quian, C.; Xie, M.; Sun, J. J. Org. Chem. 1999, 64, 6462. (j) Gadhwal, S.; Sandhu, J. S. J. Chem. Soc, Perkin Trans. 1 2000, 2827. (k) Crousse, B.; Bégué, J.-P.; Bonnet-Delpon, D. J. Org. Chem. 2000, 65, 5009. (l) Sundararajan, G.; Prabagaran, N.; Varghese, B. Org. Lett. 2001, 3, 1973. (m) Sabitha, G.; Venkata, E. R.; Yadav, J. S. Synthesis 2001, 1979. (n) Powell, D. A.; Batey, R. A. Org. Lett. 2002, 4, 2913. (o) Stevenson, P. J.; Nieuwenhuyzen, M.; Osborne, D. Chem. Commun. 2002, 444. (p) Zhang, J.; Li, C.-J. J. Org. Chem. 2002, 67, 3969. (q) Cheng, D.; Zhou, J.; Saiah, E.; Beaton, G. Org. Lett. 2002, 4, 4411. (r) Bailey, P. D.; Smith, P. D.; Morgan, K. M.; Rosair, G. M. Tetrahedron Lett. 2002, 43, 1071. (s) Hoemann, M. Z.; Xie, R. L.; Rossi, R. F.; Meyer, S.; Sidhu, A.; Cuny, G. D.; Hauske, J. R. Bioorg. Med. Chem. Lett. 2002, 12, 129. (t) Magomedov, N. A. Org. Lett. 2003, 5, 2509.
49. For leading references, see: (a) Cabral, J.; Laszlo, P. Tetrahedron Lett. 1989, 30, 7237. (b) Lucchini, V.; Prato, M.; Scorrano, G.; Stivanello, M.; Valle, G. J. Chem. Soc., Perkin Trans. 2 1992, 259. (c) Mellor, J. M.; Merriman, G. D. Tetrahedron 1995, 51, 6115. (d) Kobayashi, S.; Ishitani, H.; Nagayama, S. Synlett 1995, 1195. (e) Makioka, Y.; Shindo, T.; Taniguchi, Y.; Takaki, K.; Fujiwara, Y. Synthesis 1995, 801. (f) Baudelle, R.; Melnyck, P.; Déprez, B.; Tartar, A. Tetrahedron 1998, 54, 4125. (g) Kyselyov, A. S.; Smith, L.; Armstrong, R. W. Tetrahedron 1998, 54, 5089. (h) Babu, G.; Perumal, P. T. Tetrahedron Lett. 1998, 39, 3225. (i) Ma, Y.; Quian, C.; Xie, M.; Sun, J. J. Org. Chem. 1999, 64, 6462. (j) Gadhwal, S.; Sandhu, J. S. J. Chem. Soc, Perkin Trans. 1 2000, 2827. (k) Crousse, B.; Bégué, J.-P.; Bonnet-Delpon, D. J. Org. Chem. 2000, 65, 5009. (l) Sundararajan, G.; Prabagaran, N.; Varghese, B. Org. Lett. 2001, 3, 1973. (m) Sabitha, G.; Venkata, E. R.; Yadav, J. S. Synthesis 2001, 1979. (n) Powell, D. A.; Batey, R. A. Org. Lett. 2002, 4, 2913. (o) Stevenson, P. J.; Nieuwenhuyzen, M.; Osborne, D. Chem. Commun. 2002, 444. (p) Zhang, J.; Li, C.-J. J. Org. Chem. 2002, 67, 3969. (q) Cheng, D.; Zhou, J.; Saiah, E.; Beaton, G. Org. Lett. 2002, 4, 4411. (r) Bailey, P. D.; Smith, P. D.; Morgan, K. M.; Rosair, G. M. Tetrahedron Lett. 2002, 43, 1071. (s) Hoemann, M. Z.; Xie, R. L.; Rossi, R. F.; Meyer, S.; Sidhu, A.; Cuny, G. D.; Hauske, J. R. Bioorg. Med. Chem. Lett. 2002, 12, 129. (t) Magomedov, N. A. Org. Lett. 2003, 5, 2509.
50. For leading references, see: (a) Cabral, J.; Laszlo, P. Tetrahedron Lett. 1989, 30, 7237. (b) Lucchini, V.; Prato, M.; Scorrano, G.; Stivanello, M.; Valle, G. J. Chem. Soc., Perkin Trans. 2 1992, 259. (c) Mellor, J. M.; Merriman, G. D. Tetrahedron 1995, 51, 6115. (d) Kobayashi, S.; Ishitani, H.; Nagayama, S. Synlett 1995, 1195. (e) Makioka, Y.; Shindo, T.; Taniguchi, Y.; Takaki, K.; Fujiwara, Y. Synthesis 1995, 801. (f) Baudelle, R.; Melnyck, P.; Déprez, B.; Tartar, A. Tetrahedron 1998, 54, 4125. (g) Kyselyov, A. S.; Smith, L.; Armstrong, R. W. Tetrahedron 1998, 54, 5089. (h) Babu, G.; Perumal, P. T. Tetrahedron Lett. 1998, 39, 3225. (i) Ma, Y.; Quian, C.; Xie, M.; Sun, J. J. Org. Chem. 1999, 64, 6462. (j) Gadhwal, S.; Sandhu, J. S. J. Chem. Soc, Perkin Trans. 1 2000, 2827. (k) Crousse, B.; Bégué, J.-P.; Bonnet-Delpon, D. J. Org. Chem. 2000, 65, 5009. (l) Sundararajan, G.; Prabagaran, N.; Varghese, B. Org. Lett. 2001, 3, 1973. (m) Sabitha, G.; Venkata, E. R.; Yadav, J. S. Synthesis 2001, 1979. (n) Powell, D. A.; Batey, R. A. Org. Lett. 2002, 4, 2913. (o) Stevenson, P. J.; Nieuwenhuyzen, M.; Osborne, D. Chem. Commun. 2002, 444. (p) Zhang, J.; Li, C.-J. J. Org. Chem. 2002, 67, 3969. (q) Cheng, D.; Zhou, J.; Saiah, E.; Beaton, G. Org. Lett. 2002, 4, 4411. (r) Bailey, P. D.; Smith, P. D.; Morgan, K. M.; Rosair, G. M. Tetrahedron Lett. 2002, 43, 1071. (s) Hoemann, M. Z.; Xie, R. L.; Rossi, R. F.; Meyer, S.; Sidhu, A.; Cuny, G. D.; Hauske, J. R. Bioorg. Med. Chem. Lett. 2002, 12, 129. (t) Magomedov, N. A. Org. Lett. 2003, 5, 2509.
51. For leading references, see: (a) Cabral, J.; Laszlo, P. Tetrahedron Lett. 1989, 30, 7237. (b) Lucchini, V.; Prato, M.; Scorrano, G.; Stivanello, M.; Valle, G. J. Chem. Soc., Perkin Trans. 2 1992, 259. (c) Mellor, J. M.; Merriman, G. D. Tetrahedron 1995, 51, 6115. (d) Kobayashi, S.; Ishitani, H.; Nagayama, S. Synlett 1995, 1195. (e) Makioka, Y.; Shindo, T.; Taniguchi, Y.; Takaki, K.; Fujiwara, Y. Synthesis 1995, 801. (f) Baudelle, R.; Melnyck, P.; Déprez, B.; Tartar, A. Tetrahedron 1998, 54, 4125. (g) Kyselyov, A. S.; Smith, L.; Armstrong, R. W. Tetrahedron 1998, 54, 5089. (h) Babu, G.; Perumal, P. T. Tetrahedron Lett. 1998, 39, 3225. (i) Ma, Y.; Quian, C.; Xie, M.; Sun, J. J. Org. Chem. 1999, 64, 6462. (j) Gadhwal, S.; Sandhu, J. S. J. Chem. Soc, Perkin Trans. 1 2000, 2827. (k) Crousse, B.; Bégué, J.-P.; Bonnet-Delpon, D. J. Org. Chem. 2000, 65, 5009. (l) Sundararajan, G.; Prabagaran, N.; Varghese, B. Org. Lett. 2001, 3, 1973. (m) Sabitha, G.; Venkata, E. R.; Yadav, J. S. Synthesis 2001, 1979. (n) Powell, D. A.; Batey, R. A. Org. Lett. 2002, 4, 2913. (o) Stevenson, P. J.; Nieuwenhuyzen, M.; Osborne, D. Chem. Commun. 2002, 444. (p) Zhang, J.; Li, C.-J. J. Org. Chem. 2002, 67, 3969. (q) Cheng, D.; Zhou, J.; Saiah, E.; Beaton, G. Org. Lett. 2002, 4, 4411. (r) Bailey, P. D.; Smith, P. D.; Morgan, K. M.; Rosair, G. M. Tetrahedron Lett. 2002, 43, 1071. (s) Hoemann, M. Z.; Xie, R. L.; Rossi, R. F.; Meyer, S.; Sidhu, A.; Cuny, G. D.; Hauske, J. R. Bioorg. Med. Chem. Lett. 2002, 12, 129. (t) Magomedov, N. A. Org. Lett. 2003, 5, 2509.
52. 4 reduction of the corresponding pyridinium salts, which in turn were formed by alkylation of the commercially available pyridines.
53. (a) Taggi, A. E.; Hafez, A. M.; Lectka, T. Acc. Chem. Res. 2003, 36, 10.
54. (b) Meester, W. J. N.; van Maarseveen, J. H.; Schoemaker, H. E.; Hiemstra, H.; Rutjes, F. P. J. T. Eur. J. Org. Chem. 2003, 2519.
55. For a recent reference, see: Kumar, R. S.; Nagarajan, R.; Perumal, P. T. Synthesis 2004, 949. Also see ref 11g.
56. 3-catalyzed process, see: (a) Borrione E.; Prato, M.; Scorrano, G.; Stivanello, M.; Luccihi, V. J. Heterocycl. Chem. 1988, 25, 1831. (b) Kouznetsov, V. V.; Zubkov, F. I.; Mora Cruz, U.; Voskressensky, L. G.; Vargas Mendez, L. Y.; Astudillo, L.; Stashenko, E. E. Lett. Org. Chem. 2004, 1, 37.
57. 3-catalyzed process, see: (a) Borrione E.; Prato, M.; Scorrano, G.; Stivanello, M.; Luccihi, V. J. Heterocycl. Chem. 1988, 25, 1831. (b) Kouznetsov, V. V.; Zubkov, F. I.; Mora Cruz, U.; Voskressensky, L. G.; Vargas Mendez, L. Y.; Astudillo, L.; Stashenko, E. E. Lett. Org. Chem. 2004, 1, 37.
58. Babu, G.; Perumal, P. T. Aldrichim. Acta 2000, 33, 16.
59. (a) Kobayashi, S. Eur. J. Org. Chem. 1999, 15.
60. (b) Kobayashi, S. In Lewis Acids in Organic Synthesis; Yamamoto, H., Ed.; Wiley-VCH: Weinheim, 2000; Vol. 2, p 883.
61. (a) Itoh, T.; Nagata, K.; Kurihara, A.; Miyazaki, M.; Ohsawa, A. Tetrahedron Lett. 2002, 43, 3105.
62. (b) Itoh, T.; Nagata, K.; Kurihara, A.; Miyazaki, M.; Ishikawa, H.; Kurihara, A.; Ohsawa, A. Tetrahedron 2004, 60, 6649.
63. Fukuzumi, S.; Fujii, Y.; Suenobu, T. J. Am. Chem. Soc. 2001, 123, 10191.
64. For a preliminary account of this section, see: Lavilla, R.; Bernabeu, M. C.; Carranco, I.; Díaz, J. L. Org. Lett. 2003, 5, 717.
65. (a) Shibasaki, M.; Yamada, K.; Yoshikawa, N. In Lewis Acids in Organic Synthesis, Yamamoto, H., Ed.; Wiley-VCH: Weinheim, 2000; Vol. 2, p 911.
66. (b) Kobayashi, S.; Manabe, K. Acc. Chem. Res. 2002, 35, 209.
67. (c) Kobayashi, S.; Busujima, T.; Nagayama, S. Chem. - Eur. J. 2000, 6, 3491.
68. (d) Mikami, K.; Terada, M.; Matsuzawa, H. Angew. Chem., Int. Ed. 2002, 41, 3554.
69. 3-catalyzed reaction did not affect the yield or the stereoselectivity.
70. Spartan'02 Wavefunction, Inc., Irvine, Ca.
71. (a) Risch, N.; Arend, M. In Stereoselective Synthesis (Houben-Weyl); Helmchen, G., Hoffmann, R., Mulzer, J., Schaumann, E., Eds.; Thieme: Stuttgart, 1996; Vol. E 21, p 1925.
72. (b) For a related process, see, ref 11b.
73. (c) Hermitage, S.; Jay, D. A.; Whiting, A. Tetrahedron Lett. 2002, 43, 9633.
74. (d) Carranco, I.; Díaz, J. L.; Jiménez, O.; Lavilla, R. Tetrahedron Lett. 2003, 44, 8849.
75. (e) Also see refs 11d, and 19.
76. (a) Breslow, R. In Green Chemistry; Anastas, P. T., Williamson, T. C., Eds.; Oxford Press: New York, 1998; Chapter 13.
77. (b) For a recent reference, see: Pirrung, M. C.; Das Sarma, K. J. Am. Chem. Soc. 2004, 126, 444.
78. Manabe, K.; Aoyama, N.; Kobayashi, S. Adv. Synth. Catal. 2001, 343, 174.
79. (a) Jenner, G. Tetrahedron 1997, 53, 2669.
80. (b) van Berkom, L. W. A.; Kuster, G. J. T.; Scheeren, H. W. Mol. Diversity 2003, 6, 271.
81. The origin and the consequences of this stereochemical preference are currently being investigated.
82. For recent references, see: (a) Stadler, A.; Kappe, C. O. J. Comb. Chem. 2001, 3, 624. (b) Varma, R. S. Pure Appl. Chem. 2001, 73, 193. (c) Alexandre, F.-R.; Domon, L.; Frère, S.; Testard, A.; Thiéry, V.; Besson, T. Mol. Diversity 2003, 7, 273. (d) Blackwell, H. E. Org. Biomol. Chem. 2003, 1, 1251.
83. For recent references, see: (a) Stadler, A.; Kappe, C. O. J. Comb. Chem. 2001, 3, 624. (b) Varma, R. S. Pure Appl. Chem. 2001, 73, 193. (c) Alexandre, F.-R.; Domon, L.; Frère, S.; Testard, A.; Thiéry, V.; Besson, T. Mol. Diversity 2003, 7, 273. (d) Blackwell, H. E. Org. Biomol. Chem. 2003, 1, 1251.
84. For recent references, see: (a) Stadler, A.; Kappe, C. O. J. Comb. Chem. 2001, 3, 624. (b) Varma, R. S. Pure Appl. Chem. 2001, 73, 193. (c) Alexandre, F.-R.; Domon, L.; Frère, S.; Testard, A.; Thiéry, V.; Besson, T. Mol. Diversity 2003, 7, 273. (d) Blackwell, H. E. Org. Biomol. Chem. 2003, 1, 1251.
85. For recent references, see: (a) Stadler, A.; Kappe, C. O. J. Comb. Chem. 2001, 3, 624. (b) Varma, R. S. Pure Appl. Chem. 2001, 73, 193. (c) Alexandre, F.-R.; Domon, L.; Frère, S.; Testard, A.; Thiéry, V.; Besson, T. Mol. Diversity 2003, 7, 273. (d) Blackwell, H. E. Org. Biomol. Chem. 2003, 1, 1251.
86. The use of clays, ionic liquids or microencapsulated catalysts may constitute alternative and useful ways for catalyst immobilization. See, for instance: (a) Sartori, G.; Bigi, F.; Maggi, R.; Mazzacani, A.; Oppici, G. Eur. J. Org. Chem. 2001, 2513. (b) Yadav, J. S.; Reddy, B. V. S.; Uma Gayathri, K.; Prasad, A. R. Synthesis 2002, 2537. (c) Kobayashi, S.; Nagayama, S. J. Am. Chem. Soc. 1998, 120, 2985.
87. The use of clays, ionic liquids or microencapsulated catalysts may constitute alternative and useful ways for catalyst immobilization. See, for instance: (a) Sartori, G.; Bigi, F.; Maggi, R.; Mazzacani, A.; Oppici, G. Eur. J. Org. Chem. 2001, 2513. (b) Yadav, J. S.; Reddy, B. V. S.; Uma Gayathri, K.; Prasad, A. R. Synthesis 2002, 2537. (c) Kobayashi, S.; Nagayama, S. J. Am. Chem. Soc. 1998, 120, 2985.
88. The use of clays, ionic liquids or microencapsulated catalysts may constitute alternative and useful ways for catalyst immobilization. See, for instance: (a) Sartori, G.; Bigi, F.; Maggi, R.; Mazzacani, A.; Oppici, G. Eur. J. Org. Chem. 2001, 2513. (b) Yadav, J. S.; Reddy, B. V. S.; Uma Gayathri, K.; Prasad, A. R. Synthesis 2002, 2537. (c) Kobayashi, S.; Nagayama, S. J. Am. Chem. Soc. 1998, 120, 2985.
89. For the account of this section, see: Lavilla, R.; Carranco, I.; Díaz, J. L.; Bernabeu, M. C. Mol. Diversity 2003, 6, 171.
90. Huang, T.; Li, C.-J. Tetrahedron Lett. 2000, 41, 6715.
91. For a recent use of oxazolidine compounds as iminium ion precursors, see: Poupon, E.; François, D.; Kunesch, N.; Husson, H.-P. J. Org. Chem. 2004, 69, 3836.
92. Powell, D. A.; Batey, R. A. Tetrahedron Lett. 2003, 44, 7569.
93. (a) Pulici, M.; Cervi, G.; Martina, K.; Quartieri, F. Comb. Chem. High Throughput Screening 2003, 6, 693.
94. Also see: (b) Franzén, R. G. J. Comb. Chem. 2000, 2, 195. (c) Krchnák, V.; Holladay, M. W. Chem. Rev. 2002, 102, 61. (d) Chauhan, P. M. S.; Srivastava, S. K. Comb. Chem. High Throughput Screening 2001, 4, 35.
95. Also see: (b) Franzén, R. G. J. Comb. Chem. 2000, 2, 195. (c) Krchnák, V.; Holladay, M. W. Chem. Rev. 2002, 102, 61. (d) Chauhan, P. M. S.; Srivastava, S. K. Comb. Chem. High Throughput Screening 2001, 4, 35.
96. Also see: (b) Franzén, R. G. J. Comb. Chem. 2000, 2, 195. (c) Krchnák, V.; Holladay, M. W. Chem. Rev. 2002, 102, 61. (d) Chauhan, P. M. S.; Srivastava, S. K. Comb. Chem. High Throughput Screening 2001, 4, 35.
97. Albericio, F.; Giralt, E. In Houben-Weyl. Methods of Organic Chemistry; Synthesis of Peptides and Peptidomimetics; Goodman, M., Felix, A., Moroder, L., Toniolo, C., Eds.; Georg Thieme Verlag: Stuttgart, 2001; Vol. E 22, pp 685-709.
98. (a) Kobayashi, S.; Akiyama, R.; Kitagawa, H. J. Comb. Chem. 2001, 3, 196.
99. For alternative procedures, see: (b) Xu, Q.; Lam, K. S. Tetrahedron Lett. 2002, 43, 4435. (c) Schlienger, N.; Bryce, M. R.; Hansen, T. K. Tetrahedron Lett. 2000, 41, 5147.
100. For alternative procedures, see: (b) Xu, Q.; Lam, K. S. Tetrahedron Lett. 2002, 43, 4435. (c) Schlienger, N.; Bryce, M. R.; Hansen, T. K. Tetrahedron Lett. 2000, 41, 5147.
101. (a) Yang, L.; Guo, L Tetrahedron Lett. 1996, 37, 5041.
102. (b) Nicolás, E.; Clemente, J.; Ferrer, T.; Albericio, F.; Giralt, E. Tetrahedron 1997, 53, 3179.
103. Taylor, S. J.; Taylor, A. M.; Schreiber, S. L. Angew. Chem., Int. Ed. 2004, 43, 1681.