A stereoselective route towards highly functionalized 4,6-diaminocyclohexene derivatives

Tetrahedron Letters

Volumn 43, Issue 36, 2002, Pages 6451-6455

  Verhelst, Steven H L ^a   Wiedenhof, Wouter ^a   Ovaa, Huib ^a   Van Der Marel, Gijsbert A ^a   Overkleeft, Herman S ^a   Van Boeckel, Constant A A ^b   Van Boom, Jacques H ^a  

^a LEIDEN UNIVERSITY   (Netherlands)

^b NV ORGANON   (Netherlands)

Author keywords

[No Author keywords available]

Indexed keywords

CARBOHYDRATE; CYCLOHEXENE DERIVATIVE; PALLADIUM;

AMINATION; ARTICLE; CATALYST; DRUG SYNTHESIS; ENANTIOMER; RING CLOSING METATHESIS; STEREOCHEMISTRY;

EID: 0037009728     PISSN: 00404039     EISSN: None     Source Type: Journal    
DOI: 10.1016/S0040-4039(02)01364-3     Document Type: Article

References (33)

1. Moazed D., Noller H.F. Nature. 327:1987;389-394.
2. Puhorit P., Stern S. Nature. 370:1994;659-662.
3. Zapp M.L., Stern S., Green M.R. Cell. 74:1993;969-978.
4. Mei H.-Y., Mack D.P., Galan A.A., Halim N.S., Heldsinger A., Loo J.A., Moreland D.W., Sannes-Lowery K.A., Sharmeen L., Truong H.N., Czarnik A.W. Bioorg. Med. Chem. 5:1997;1173-1184.
5. See for recent reviews on aminoglycosides: (a) Gallego, J.; Varani, G. Acc. Chem. Res. 2001, 34, 836-843; (b) Kotra, L. P.; Mobashery, S. Curr. Org. Chem. 2001, 5, 193-205; (c) Wilson, W. D.; Li, K. Curr. Med. Chem. 2000, 7, 73-98; (d) Hermann, T. Angew. Chem., Int. Ed. 2000, 39, 1890-1905; (e) Schroeder, R.; Waldsich, C.; Wank, H. EMBO J. 2000, 19, 1-9; (f) Sucheck, S. J.; Wong, C.-H. Curr. Opin. Chem. Biol. 2000, 4, 678-686.
6. See for recent reviews on aminoglycosides: (a) Gallego, J.; Varani, G. Acc. Chem. Res. 2001, 34, 836-843; (b) Kotra, L. P.; Mobashery, S. Curr. Org. Chem. 2001, 5, 193-205; (c) Wilson, W. D.; Li, K. Curr. Med. Chem. 2000, 7, 73-98; (d) Hermann, T. Angew. Chem., Int. Ed. 2000, 39, 1890-1905; (e) Schroeder, R.; Waldsich, C.; Wank, H. EMBO J. 2000, 19, 1-9; (f) Sucheck, S. J.; Wong, C.-H. Curr. Opin. Chem. Biol. 2000, 4, 678-686.
7. See for recent reviews on aminoglycosides: (a) Gallego, J.; Varani, G. Acc. Chem. Res. 2001, 34, 836-843; (b) Kotra, L. P.; Mobashery, S. Curr. Org. Chem. 2001, 5, 193-205; (c) Wilson, W. D.; Li, K. Curr. Med. Chem. 2000, 7, 73-98; (d) Hermann, T. Angew. Chem., Int. Ed. 2000, 39, 1890-1905; (e) Schroeder, R.; Waldsich, C.; Wank, H. EMBO J. 2000, 19, 1-9; (f) Sucheck, S. J.; Wong, C.-H. Curr. Opin. Chem. Biol. 2000, 4, 678-686.
8. See for recent reviews on aminoglycosides: (a) Gallego, J.; Varani, G. Acc. Chem. Res. 2001, 34, 836-843; (b) Kotra, L. P.; Mobashery, S. Curr. Org. Chem. 2001, 5, 193-205; (c) Wilson, W. D.; Li, K. Curr. Med. Chem. 2000, 7, 73-98; (d) Hermann, T. Angew. Chem., Int. Ed. 2000, 39, 1890-1905; (e) Schroeder, R.; Waldsich, C.; Wank, H. EMBO J. 2000, 19, 1-9; (f) Sucheck, S. J.; Wong, C.-H. Curr. Opin. Chem. Biol. 2000, 4, 678-686.
9. See for recent reviews on aminoglycosides: (a) Gallego, J.; Varani, G. Acc. Chem. Res. 2001, 34, 836-843; (b) Kotra, L. P.; Mobashery, S. Curr. Org. Chem. 2001, 5, 193-205; (c) Wilson, W. D.; Li, K. Curr. Med. Chem. 2000, 7, 73-98; (d) Hermann, T. Angew. Chem., Int. Ed. 2000, 39, 1890-1905; (e) Schroeder, R.; Waldsich, C.; Wank, H. EMBO J. 2000, 19, 1-9; (f) Sucheck, S. J.; Wong, C.-H. Curr. Opin. Chem. Biol. 2000, 4, 678-686.
10. See for recent reviews on aminoglycosides: (a) Gallego, J.; Varani, G. Acc. Chem. Res. 2001, 34, 836-843; (b) Kotra, L. P.; Mobashery, S. Curr. Org. Chem. 2001, 5, 193-205; (c) Wilson, W. D.; Li, K. Curr. Med. Chem. 2000, 7, 73-98; (d) Hermann, T. Angew. Chem., Int. Ed. 2000, 39, 1890-1905; (e) Schroeder, R.; Waldsich, C.; Wank, H. EMBO J. 2000, 19, 1-9; (f) Sucheck, S. J.; Wong, C.-H. Curr. Opin. Chem. Biol. 2000, 4, 678-686.
11. Zembower T.R., Noskin G.A., Postelnick M.J., Nguyen C., Peterson L.R. Int. J. Antimicrob. Ag. 10:1998;95-105.
12. Mingeot-Leclercq M.-P., Glupczynski Y., Tulkens P.M. Antimicrob. Agents Chemother. 43:1999;727-737.
13. Mingeot-Leclercq M.-P., Tulkens P.M. Antimicrob. Agents Chemother. 43:1999;1003-1012.
14. See for example: (a) Georgiadis, M. P.; Constantinou-Kokotou, V.; Kokotos, G. J. Carbohydr. Chem. 1991, 10, 739-748; (b) Park, W. K. C.; Auer, M.; Jaksche, H.; Wong, C.-H. J. Am. Chem. Soc. 1996, 48, 10150-10155; (c) Kirk, S. R.; Luedtke, N. W.; Tor, Y. J. Am. Chem. Soc. 2000, 122, 980-981; (d) Hamasaki, K.; Woo, M.-C.; Ueno, A. Tetrahedron Lett. 2000, 41, 8327-8332; (e) Nunns, C. L.; Spence, L. A.; Slater, M. J.; Berrisford, D. J. Tetrahedron Lett. 1999, 40, 9341-9345; (f) Haddad, J.; Kotra, L. P.; Llano-Sotelo, B.; Kim, C.; Azucena, E. F., Jr.; Liu, M.; Vakulenko, S. B.; Chow, C. S.; Mobashery, S. J. Am. Chem. Soc. 2002, 124, 3229-3237.
15. See for example: (a) Georgiadis, M. P.; Constantinou-Kokotou, V.; Kokotos, G. J. Carbohydr. Chem. 1991, 10, 739-748; (b) Park, W. K. C.; Auer, M.; Jaksche, H.; Wong, C.-H. J. Am. Chem. Soc. 1996, 48, 10150-10155; (c) Kirk, S. R.; Luedtke, N. W.; Tor, Y. J. Am. Chem. Soc. 2000, 122, 980-981; (d) Hamasaki, K.; Woo, M.-C.; Ueno, A. Tetrahedron Lett. 2000, 41, 8327-8332; (e) Nunns, C. L.; Spence, L. A.; Slater, M. J.; Berrisford, D. J. Tetrahedron Lett. 1999, 40, 9341-9345; (f) Haddad, J.; Kotra, L. P.; Llano-Sotelo, B.; Kim, C.; Azucena, E. F., Jr.; Liu, M.; Vakulenko, S. B.; Chow, C. S.; Mobashery, S. J. Am. Chem. Soc. 2002, 124, 3229-3237.
16. See for example: (a) Georgiadis, M. P.; Constantinou-Kokotou, V.; Kokotos, G. J. Carbohydr. Chem. 1991, 10, 739-748; (b) Park, W. K. C.; Auer, M.; Jaksche, H.; Wong, C.-H. J. Am. Chem. Soc. 1996, 48, 10150-10155; (c) Kirk, S. R.; Luedtke, N. W.; Tor, Y. J. Am. Chem. Soc. 2000, 122, 980-981; (d) Hamasaki, K.; Woo, M.-C.; Ueno, A. Tetrahedron Lett. 2000, 41, 8327-8332; (e) Nunns, C. L.; Spence, L. A.; Slater, M. J.; Berrisford, D. J. Tetrahedron Lett. 1999, 40, 9341-9345; (f) Haddad, J.; Kotra, L. P.; Llano-Sotelo, B.; Kim, C.; Azucena, E. F., Jr.; Liu, M.; Vakulenko, S. B.; Chow, C. S.; Mobashery, S. J. Am. Chem. Soc. 2002, 124, 3229-3237.
17. See for example: (a) Georgiadis, M. P.; Constantinou-Kokotou, V.; Kokotos, G. J. Carbohydr. Chem. 1991, 10, 739-748; (b) Park, W. K. C.; Auer, M.; Jaksche, H.; Wong, C.-H. J. Am. Chem. Soc. 1996, 48, 10150-10155; (c) Kirk, S. R.; Luedtke, N. W.; Tor, Y. J. Am. Chem. Soc. 2000, 122, 980-981; (d) Hamasaki, K.; Woo, M.-C.; Ueno, A. Tetrahedron Lett. 2000, 41, 8327-8332; (e) Nunns, C. L.; Spence, L. A.; Slater, M. J.; Berrisford, D. J. Tetrahedron Lett. 1999, 40, 9341-9345; (f) Haddad, J.; Kotra, L. P.; Llano-Sotelo, B.; Kim, C.; Azucena, E. F., Jr.; Liu, M.; Vakulenko, S. B.; Chow, C. S.; Mobashery, S. J. Am. Chem. Soc. 2002, 124, 3229-3237.
18. See for example: (a) Georgiadis, M. P.; Constantinou-Kokotou, V.; Kokotos, G. J. Carbohydr. Chem. 1991, 10, 739-748; (b) Park, W. K. C.; Auer, M.; Jaksche, H.; Wong, C.-H. J. Am. Chem. Soc. 1996, 48, 10150-10155; (c) Kirk, S. R.; Luedtke, N. W.; Tor, Y. J. Am. Chem. Soc. 2000, 122, 980-981; (d) Hamasaki, K.; Woo, M.-C.; Ueno, A. Tetrahedron Lett. 2000, 41, 8327-8332; (e) Nunns, C. L.; Spence, L. A.; Slater, M. J.; Berrisford, D. J. Tetrahedron Lett. 1999, 40, 9341-9345; (f) Haddad, J.; Kotra, L. P.; Llano-Sotelo, B.; Kim, C.; Azucena, E. F., Jr.; Liu, M.; Vakulenko, S. B.; Chow, C. S.; Mobashery, S. J. Am. Chem. Soc. 2002, 124, 3229-3237.
19. See for example: (a) Georgiadis, M. P.; Constantinou-Kokotou, V.; Kokotos, G. J. Carbohydr. Chem. 1991, 10, 739-748; (b) Park, W. K. C.; Auer, M.; Jaksche, H.; Wong, C.-H. J. Am. Chem. Soc. 1996, 48, 10150-10155; (c) Kirk, S. R.; Luedtke, N. W.; Tor, Y. J. Am. Chem. Soc. 2000, 122, 980-981; (d) Hamasaki, K.; Woo, M.-C.; Ueno, A. Tetrahedron Lett. 2000, 41, 8327-8332; (e) Nunns, C. L.; Spence, L. A.; Slater, M. J.; Berrisford, D. J. Tetrahedron Lett. 1999, 40, 9341-9345; (f) Haddad, J.; Kotra, L. P.; Llano-Sotelo, B.; Kim, C.; Azucena, E. F., Jr.; Liu, M.; Vakulenko, S. B.; Chow, C. S.; Mobashery, S. J. Am. Chem. Soc. 2002, 124, 3229-3237.
20. Hermann T., Westhof E. J. Med. Chem. 42:1999;1250-1261.
21. Hyldtoft L., Poulsen C.S., Madsen R. Chem. Commun. 1999;2101-2102.
22. Hyldtoft L., Madsen R. J. Am. Chem. Soc. 122:2000;8444-8452.
23. 3).
24. Fukuyama T., Jow C.-K., Cheung M. Tetrahedron Lett. 36:1995;6373-6374.
25. Schwab P., France M.B., Ziller J.W., Grubbs R.H. Angew. Chem., Int. Ed. Engl. 34:1995;2039-2041.
26. Grubbs R.H., Chang S. Tetrahedron. 54:1998;4413-4450.
27. Upon substitution, the cyclic carbonate liberates carbon dioxide and generates an allylic alcohol which is not susceptible for further reaction. The corresponding bis-acetates did not react in palladium catalyzed allylic aminations.
28. 3 (25 mol%) were added, and the reaction mixture was stirred under argon for 3 h at ambient temperature. The reaction mixture was concentrated in vacuo and purified by flash chromatography, affording the desired products as slightly yellow foams.
29. Dppb: diphenylphospinobutane; dppp: diphenylphosphinopropane.
30. 2 proceeded in 22 and 27% yield, respectively. The yield could not be improved by performing the reaction at elevated temperature (50°C).
31. Evans M.E., Parish F.W. Methods Carbohydr. Chem. 8:1980;173.
32. Veeneman G.H., Gomes L.J.F., van Boom J.H. Tetrahedron. 45:1989;7433-7448.
33. Kissman H.M., Baker B.R. J. Am. Chem. Soc. 79:1957;5534-5540.