Stereochemical control of the passerini reaction

Organic Letters

Volumn 6, Issue 23, 2004, Pages 4231-4233

  Andreana, Peter R ^a   Liu, Chang C ^a   Schreiber, Stuart L ^a  

^a HARVARD UNIVERSITY   (United States)

Author keywords

[No Author keywords available]

Indexed keywords

ARTICLE; CATALYSIS; CHEMICAL REACTION; ENANTIOSELECTIVITY; HIGH PERFORMANCE LIQUID CHROMATOGRAPHY; PASSERINI REACTION; STEREOCHEMISTRY; X RAY CRYSTALLOGRAPHY;

EID: 9444230492     PISSN: 15237060     EISSN: None     Source Type: Journal    
DOI: 10.1021/ol0482893     Document Type: Article

References (28)

1. (a) Schreiber, S. L. Science 2000, 287, 1964-1969.
2. (b) Schreiber, S. L. Chem. Eng. News 2003, 81, 51-61.
3. Burke, M. D.; Schreiber, S. L. Angew. Chem., Int. Ed. 2004, 43, 46-58.
4. (a) Burke, M. D.; Berger, E, M.; Schreiber, S. L. Science 2003, 302, 613-616.
5. (b) Sello, J. K.; Andreana, P. R.; Lee, D.; Schreiber, S. L. Org. Lett. 2003, 5, 4125-4127.
6. For recent reviews: (a) von Wangelin, A. J.; Neumann, H.; Goerdes, D.; Klaus, S.; Struebing, D.; Beller, M. Chem. Eur. J. 2003, 9, 4286-4294. (b) Ugi, L.; Werner, B.; Doemling, A. Molecules 2003, 8, 53-66. (c) Domling, A. Curr. Opin. Chem. Biol. 2002, 6, 306-313. (d) Domling, A.; Ugi, I. Angew. Chem., Int. Ed. 2000, 39, 3168-3210. (e) Bienayme, H.; Hulme, C.; Oddon, G.; Schmitt, P. Chem. Eur. J. 2000, 6, 3321-3329.
7. For recent reviews: (a) von Wangelin, A. J.; Neumann, H.; Goerdes, D.; Klaus, S.; Struebing, D.; Beller, M. Chem. Eur. J. 2003, 9, 4286-4294. (b) Ugi, L.; Werner, B.; Doemling, A. Molecules 2003, 8, 53-66. (c) Domling, A. Curr. Opin. Chem. Biol. 2002, 6, 306-313. (d) Domling, A.; Ugi, I. Angew. Chem., Int. Ed. 2000, 39, 3168-3210. (e) Bienayme, H.; Hulme, C.; Oddon, G.; Schmitt, P. Chem. Eur. J. 2000, 6, 3321-3329.
8. For recent reviews: (a) von Wangelin, A. J.; Neumann, H.; Goerdes, D.; Klaus, S.; Struebing, D.; Beller, M. Chem. Eur. J. 2003, 9, 4286-4294. (b) Ugi, L.; Werner, B.; Doemling, A. Molecules 2003, 8, 53-66. (c) Domling, A. Curr. Opin. Chem. Biol. 2002, 6, 306-313. (d) Domling, A.; Ugi, I. Angew. Chem., Int. Ed. 2000, 39, 3168-3210. (e) Bienayme, H.; Hulme, C.; Oddon, G.; Schmitt, P. Chem. Eur. J. 2000, 6, 3321-3329.
9. For recent reviews: (a) von Wangelin, A. J.; Neumann, H.; Goerdes, D.; Klaus, S.; Struebing, D.; Beller, M. Chem. Eur. J. 2003, 9, 4286-4294. (b) Ugi, L.; Werner, B.; Doemling, A. Molecules 2003, 8, 53-66. (c) Domling, A. Curr. Opin. Chem. Biol. 2002, 6, 306-313. (d) Domling, A.; Ugi, I. Angew. Chem., Int. Ed. 2000, 39, 3168-3210. (e) Bienayme, H.; Hulme, C.; Oddon, G.; Schmitt, P. Chem. Eur. J. 2000, 6, 3321-3329.
10. For recent reviews: (a) von Wangelin, A. J.; Neumann, H.; Goerdes, D.; Klaus, S.; Struebing, D.; Beller, M. Chem. Eur. J. 2003, 9, 4286-4294. (b) Ugi, L.; Werner, B.; Doemling, A. Molecules 2003, 8, 53-66. (c) Domling, A. Curr. Opin. Chem. Biol. 2002, 6, 306-313. (d) Domling, A.; Ugi, I. Angew. Chem., Int. Ed. 2000, 39, 3168-3210. (e) Bienayme, H.; Hulme, C.; Oddon, G.; Schmitt, P. Chem. Eur. J. 2000, 6, 3321-3329.
11. Diastereoselective multicomponent coupling reactions: (a) Cuny, G.; Gamez-Montano, R.; Zhu, J.; Tetrahedron 2004, 60, 4879-4885. (b) Frey, R.; Galbraith, S. F.; Guelfi, S.; Lamberth, C.; Zeller, M. Synlett 2003, 1536-1538. (c) Ross, G. F.; Herdtweck, E.; Ugi, I. Tetrahedron 2002, 58, 6127-6133. (d) Oertel, K.; Zech, G.; Kunz, H. Angew. Chem., Int. Ed. 2000, 39, 1431-1433. (e) Ziegler, T.; Kaisers, H.-J.; Schlomer, R.; Koch, C. Tetrahedron 1999, 55, 8397-8408. (f) Linderman, R. J.; Binet, S.; Petrich, S. R. J. Org. Chem. 1999, 64, 336-337. (g) Bock, H.; Ugi, I. J. Prakt. Chem. 1997, 339, 385-389. (h) Semple, J. E.; Wang, P. C.; Lysenko, Z.; Joullie, M. M. J. Am. Chem. Soc. 1980, 102, 7505-7510. (i) Ugi, I.; Offermann, K.; Herlinger, H.; Marquarding, D. Liebigs. Ann. Chem. 1967, 709, 1-10. (j) Ugi, I.; Offermann, K. Angew. Chem. 1963, 75, 917.
12. Diastereoselective multicomponent coupling reactions: (a) Cuny, G.; Gamez-Montano, R.; Zhu, J.; Tetrahedron 2004, 60, 4879-4885. (b) Frey, R.; Galbraith, S. F.; Guelfi, S.; Lamberth, C.; Zeller, M. Synlett 2003, 1536-1538. (c) Ross, G. F.; Herdtweck, E.; Ugi, I. Tetrahedron 2002, 58, 6127-6133. (d) Oertel, K.; Zech, G.; Kunz, H. Angew. Chem., Int. Ed. 2000, 39, 1431-1433. (e) Ziegler, T.; Kaisers, H.-J.; Schlomer, R.; Koch, C. Tetrahedron 1999, 55, 8397-8408. (f) Linderman, R. J.; Binet, S.; Petrich, S. R. J. Org. Chem. 1999, 64, 336-337. (g) Bock, H.; Ugi, I. J. Prakt. Chem. 1997, 339, 385-389. (h) Semple, J. E.; Wang, P. C.; Lysenko, Z.; Joullie, M. M. J. Am. Chem. Soc. 1980, 102, 7505-7510. (i) Ugi, I.; Offermann, K.; Herlinger, H.; Marquarding, D. Liebigs. Ann. Chem. 1967, 709, 1-10. (j) Ugi, I.; Offermann, K. Angew. Chem. 1963, 75, 917.
13. Diastereoselective multicomponent coupling reactions: (a) Cuny, G.; Gamez-Montano, R.; Zhu, J.; Tetrahedron 2004, 60, 4879-4885. (b) Frey, R.; Galbraith, S. F.; Guelfi, S.; Lamberth, C.; Zeller, M. Synlett 2003, 1536-1538. (c) Ross, G. F.; Herdtweck, E.; Ugi, I. Tetrahedron 2002, 58, 6127-6133. (d) Oertel, K.; Zech, G.; Kunz, H. Angew. Chem., Int. Ed. 2000, 39, 1431-1433. (e) Ziegler, T.; Kaisers, H.-J.; Schlomer, R.; Koch, C. Tetrahedron 1999, 55, 8397-8408. (f) Linderman, R. J.; Binet, S.; Petrich, S. R. J. Org. Chem. 1999, 64, 336-337. (g) Bock, H.; Ugi, I. J. Prakt. Chem. 1997, 339, 385-389. (h) Semple, J. E.; Wang, P. C.; Lysenko, Z.; Joullie, M. M. J. Am. Chem. Soc. 1980, 102, 7505-7510. (i) Ugi, I.; Offermann, K.; Herlinger, H.; Marquarding, D. Liebigs. Ann. Chem. 1967, 709, 1-10. (j) Ugi, I.; Offermann, K. Angew. Chem. 1963, 75, 917.
14. Diastereoselective multicomponent coupling reactions: (a) Cuny, G.; Gamez-Montano, R.; Zhu, J.; Tetrahedron 2004, 60, 4879-4885. (b) Frey, R.; Galbraith, S. F.; Guelfi, S.; Lamberth, C.; Zeller, M. Synlett 2003, 1536-1538. (c) Ross, G. F.; Herdtweck, E.; Ugi, I. Tetrahedron 2002, 58, 6127-6133. (d) Oertel, K.; Zech, G.; Kunz, H. Angew. Chem., Int. Ed. 2000, 39, 1431-1433. (e) Ziegler, T.; Kaisers, H.-J.; Schlomer, R.; Koch, C. Tetrahedron 1999, 55, 8397-8408. (f) Linderman, R. J.; Binet, S.; Petrich, S. R. J. Org. Chem. 1999, 64, 336-337. (g) Bock, H.; Ugi, I. J. Prakt. Chem. 1997, 339, 385-389. (h) Semple, J. E.; Wang, P. C.; Lysenko, Z.; Joullie, M. M. J. Am. Chem. Soc. 1980, 102, 7505-7510. (i) Ugi, I.; Offermann, K.; Herlinger, H.; Marquarding, D. Liebigs. Ann. Chem. 1967, 709, 1-10. (j) Ugi, I.; Offermann, K. Angew. Chem. 1963, 75, 917.
15. Diastereoselective multicomponent coupling reactions: (a) Cuny, G.; Gamez-Montano, R.; Zhu, J.; Tetrahedron 2004, 60, 4879-4885. (b) Frey, R.; Galbraith, S. F.; Guelfi, S.; Lamberth, C.; Zeller, M. Synlett 2003, 1536-1538. (c) Ross, G. F.; Herdtweck, E.; Ugi, I. Tetrahedron 2002, 58, 6127-6133. (d) Oertel, K.; Zech, G.; Kunz, H. Angew. Chem., Int. Ed. 2000, 39, 1431-1433. (e) Ziegler, T.; Kaisers, H.-J.; Schlomer, R.; Koch, C. Tetrahedron 1999, 55, 8397-8408. (f) Linderman, R. J.; Binet, S.; Petrich, S. R. J. Org. Chem. 1999, 64, 336-337. (g) Bock, H.; Ugi, I. J. Prakt. Chem. 1997, 339, 385-389. (h) Semple, J. E.; Wang, P. C.; Lysenko, Z.; Joullie, M. M. J. Am. Chem. Soc. 1980, 102, 7505-7510. (i) Ugi, I.; Offermann, K.; Herlinger, H.; Marquarding, D. Liebigs. Ann. Chem. 1967, 709, 1-10. (j) Ugi, I.; Offermann, K. Angew. Chem. 1963, 75, 917.
16. Diastereoselective multicomponent coupling reactions: (a) Cuny, G.; Gamez-Montano, R.; Zhu, J.; Tetrahedron 2004, 60, 4879-4885. (b) Frey, R.; Galbraith, S. F.; Guelfi, S.; Lamberth, C.; Zeller, M. Synlett 2003, 1536-1538. (c) Ross, G. F.; Herdtweck, E.; Ugi, I. Tetrahedron 2002, 58, 6127-6133. (d) Oertel, K.; Zech, G.; Kunz, H. Angew. Chem., Int. Ed. 2000, 39, 1431-1433. (e) Ziegler, T.; Kaisers, H.-J.; Schlomer, R.; Koch, C. Tetrahedron 1999, 55, 8397-8408. (f) Linderman, R. J.; Binet, S.; Petrich, S. R. J. Org. Chem. 1999, 64, 336-337. (g) Bock, H.; Ugi, I. J. Prakt. Chem. 1997, 339, 385-389. (h) Semple, J. E.; Wang, P. C.; Lysenko, Z.; Joullie, M. M. J. Am. Chem. Soc. 1980, 102, 7505-7510. (i) Ugi, I.; Offermann, K.; Herlinger, H.; Marquarding, D. Liebigs. Ann. Chem. 1967, 709, 1-10. (j) Ugi, I.; Offermann, K. Angew. Chem. 1963, 75, 917.
17. Diastereoselective multicomponent coupling reactions: (a) Cuny, G.; Gamez-Montano, R.; Zhu, J.; Tetrahedron 2004, 60, 4879-4885. (b) Frey, R.; Galbraith, S. F.; Guelfi, S.; Lamberth, C.; Zeller, M. Synlett 2003, 1536-1538. (c) Ross, G. F.; Herdtweck, E.; Ugi, I. Tetrahedron 2002, 58, 6127-6133. (d) Oertel, K.; Zech, G.; Kunz, H. Angew. Chem., Int. Ed. 2000, 39, 1431-1433. (e) Ziegler, T.; Kaisers, H.-J.; Schlomer, R.; Koch, C. Tetrahedron 1999, 55, 8397-8408. (f) Linderman, R. J.; Binet, S.; Petrich, S. R. J. Org. Chem. 1999, 64, 336-337. (g) Bock, H.; Ugi, I. J. Prakt. Chem. 1997, 339, 385-389. (h) Semple, J. E.; Wang, P. C.; Lysenko, Z.; Joullie, M. M. J. Am. Chem. Soc. 1980, 102, 7505-7510. (i) Ugi, I.; Offermann, K.; Herlinger, H.; Marquarding, D. Liebigs. Ann. Chem. 1967, 709, 1-10. (j) Ugi, I.; Offermann, K. Angew. Chem. 1963, 75, 917.
18. Diastereoselective multicomponent coupling reactions: (a) Cuny, G.; Gamez-Montano, R.; Zhu, J.; Tetrahedron 2004, 60, 4879-4885. (b) Frey, R.; Galbraith, S. F.; Guelfi, S.; Lamberth, C.; Zeller, M. Synlett 2003, 1536-1538. (c) Ross, G. F.; Herdtweck, E.; Ugi, I. Tetrahedron 2002, 58, 6127-6133. (d) Oertel, K.; Zech, G.; Kunz, H. Angew. Chem., Int. Ed. 2000, 39, 1431-1433. (e) Ziegler, T.; Kaisers, H.-J.; Schlomer, R.; Koch, C. Tetrahedron 1999, 55, 8397-8408. (f) Linderman, R. J.; Binet, S.; Petrich, S. R. J. Org. Chem. 1999, 64, 336-337. (g) Bock, H.; Ugi, I. J. Prakt. Chem. 1997, 339, 385-389. (h) Semple, J. E.; Wang, P. C.; Lysenko, Z.; Joullie, M. M. J. Am. Chem. Soc. 1980, 102, 7505-7510. (i) Ugi, I.; Offermann, K.; Herlinger, H.; Marquarding, D. Liebigs. Ann. Chem. 1967, 709, 1-10. (j) Ugi, I.; Offermann, K. Angew. Chem. 1963, 75, 917.
19. Diastereoselective multicomponent coupling reactions: (a) Cuny, G.; Gamez-Montano, R.; Zhu, J.; Tetrahedron 2004, 60, 4879-4885. (b) Frey, R.; Galbraith, S. F.; Guelfi, S.; Lamberth, C.; Zeller, M. Synlett 2003, 1536-1538. (c) Ross, G. F.; Herdtweck, E.; Ugi, I. Tetrahedron 2002, 58, 6127-6133. (d) Oertel, K.; Zech, G.; Kunz, H. Angew. Chem., Int. Ed. 2000, 39, 1431-1433. (e) Ziegler, T.; Kaisers, H.-J.; Schlomer, R.; Koch, C. Tetrahedron 1999, 55, 8397-8408. (f) Linderman, R. J.; Binet, S.; Petrich, S. R. J. Org. Chem. 1999, 64, 336-337. (g) Bock, H.; Ugi, I. J. Prakt. Chem. 1997, 339, 385-389. (h) Semple, J. E.; Wang, P. C.; Lysenko, Z.; Joullie, M. M. J. Am. Chem. Soc. 1980, 102, 7505-7510. (i) Ugi, I.; Offermann, K.; Herlinger, H.; Marquarding, D. Liebigs. Ann. Chem. 1967, 709, 1-10. (j) Ugi, I.; Offermann, K. Angew. Chem. 1963, 75, 917.
20. Diastereoselective multicomponent coupling reactions: (a) Cuny, G.; Gamez-Montano, R.; Zhu, J.; Tetrahedron 2004, 60, 4879-4885. (b) Frey, R.; Galbraith, S. F.; Guelfi, S.; Lamberth, C.; Zeller, M. Synlett 2003, 1536-1538. (c) Ross, G. F.; Herdtweck, E.; Ugi, I. Tetrahedron 2002, 58, 6127-6133. (d) Oertel, K.; Zech, G.; Kunz, H. Angew. Chem., Int. Ed. 2000, 39, 1431-1433. (e) Ziegler, T.; Kaisers, H.-J.; Schlomer, R.; Koch, C. Tetrahedron 1999, 55, 8397-8408. (f) Linderman, R. J.; Binet, S.; Petrich, S. R. J. Org. Chem. 1999, 64, 336-337. (g) Bock, H.; Ugi, I. J. Prakt. Chem. 1997, 339, 385-389. (h) Semple, J. E.; Wang, P. C.; Lysenko, Z.; Joullie, M. M. J. Am. Chem. Soc. 1980, 102, 7505-7510. (i) Ugi, I.; Offermann, K.; Herlinger, H.; Marquarding, D. Liebigs. Ann. Chem. 1967, 709, 1-10. (j) Ugi, I.; Offermann, K. Angew. Chem. 1963, 75, 917.
21. Kusebauch, U.; Beck, B.; Messer, K.; Herdtweck, E.; Domling, A. Org. Lett. 2003, 5, 4021-4024.
22. For the Passerini-type reaction giving rise to α- hydroxycarboxamide: Denmark, S. E.; Fan, Y. J. Am. Chem. Soc. 2003, 125, 7825-7827.
23. (a) Evans, D. A.; Rovis, T.; Johnson, J. S. Pure Appl. Chem. 1999, 71, 1407-1415.
24. (b) Evans, D. A.; Kozlowski, M. C.; Murry, J. A.; Burgey, C. S.; Connell, B.; Staples, R. J. J. Am. Chem. Soc. 1999, 121, 669-685.
25. Stavenger, R. A.; Schreiber, S. L. Angew. Chem., Int. Ed. 2001, 40, 3417-3421.
26. For the synthesis of pybox ligand 4: Davies, I. W.; Gerena, L.; Lu, N.; Larsen, R. D.; Reider, P. J. J. Am. Chem. Soc. 1996, 61, 9629-9630.
27. (a) Pirrung, M. C.; Sarma, K. D. J. Am. Chem. Soc. 2004, 126, 444-445.
28. (b) de Nooy, A. E. J.; Masci, G.; Crescenzi, V. Macromolecules 1999, 32, 1318-1320.