An enantioselective organocatalytic route to chiral 3,6-dihydropyridazines from aldehydes

Synlett

Volumn , Issue 16, 2006, Pages 2548-2552

  Oelke, Alexander J ^a   Kumarn, Sirirat ^a   Longbottom, Deborah A ^a   Ley, Steven V ^a  

^a UNIVERSITY OF CAMBRIDGE   (United Kingdom)

Author keywords

Asymmetric catalysis; Heterocycles; Ring closure; Tandem reactions; Wittig reaction

Indexed keywords

ALDEHYDE; PYRIDAZINE DERIVATIVE;

ARTICLE; CATALYSIS; ENANTIOSELECTIVITY; SYNTHESIS;

EID: 33750040576     PISSN: 09365214     EISSN: None     Source Type: Journal    
DOI: 10.1055/s-2006-951486     Document Type: Article

References (52)

1. For a review about piperazic acids, see: (a) Ciufolini, M. A.; Xi, N. Chem. Soc. Rev. 1998, 27, 437.
2. (b) Hale, K. J.; Cai, J.; Delisser, V.; Manaviazar, S.; Peak, S. A.; Bhatia, G. S.; Collins, T. C.; Jogiya, N. Tetrahedron 1996, 52, 1047.
3. Williams, P. D.; Bock, M. G.; Tung, R. D.; Garsky, V. M.; Perlow, D. S.; Erb, J. M.; Lundell, G. F.; Gould, N. P.; Whitter, W. L.; Hoffman, J. B.; Kaufman, M. J.; Clineschmidt, B. V.; Pettibone, D. J.; Freidinger, R. M.; Veber, D. F. J. Med. Chem. 1992, 35, 3905.
4. (a) Morimoto, K.; Shimada, N.; Naganawa, H.; Takita, T.; Umezawa, H. J. Antibiot. 1981, 34, 1615.
5. (b) Morimoto, K.; Shimada, N.; Naganawa, H.; Takita, T.; Umezawa, H. J. Antibiot. 1982, 35, 378.
6. (a) Hassall, C. H.; Johnson, W. H.; Theobald, C. J. J. Chem. Soc., Perkin Trans. 1 1979, 1451.
7. (b) Davies, C. R.; Davies, J. S. J. Chem. Soc., Perkin Trans. 1 1976, 2390.
8. (c) Aspinall, I. H.; Cowley, P. M.; Mitchell, G.; Stoodley, R. J. J. Chem. Soc., Chem. Commun. 1993, 1179.
9. (d) Aspinall, I. H.; Cowley, P. M.; Mitchell, G.; Raynor, C. M.; Stoodley, R. J. J. Chem. Soc., Perkin Trans. 1 1999, 2591.
10. (e) Makino, K.; Henmi, Y.; Terasawa, M.; Hara, O.; Hamada, Y. Tetrahedron Lett. 2005, 46, 555.
11. (a) Ciufolini, M. A.; Shimizu, T.; Swaminathan, S.; Xi, N. Tetrahedron Lett. 1997, 43, 891.
12. (b) Vidal, J.; Damestoy, S.; Guy, L.; Hannachi, J.-C.; Aubry, A.; Collet, A. Chem. Eur. J. 1997, 3, 1691.
13. (c) Hannachi, J.-C.; Vidal, J.; Mulatier, J.-C.; Collet, A. J. Org. Chem. 2004, 69, 2367.
14. Schmidt, U.; Braun, C.; Sutoris, H. Synthesis 1996, 223.
15. (a) Hughes, P.; Clardy, J. J. Org. Chem. 1989, 54, 3260.
16. (b) Hughes, P.; Clardy, J. J. Org. Chem. 1995, 60, 2950.
17. (a) Nakamura, Y.; Shin, C.-G. Chem. Lett. 1991, 1953.
18. (b) Schmidt, U.; Reidl, B. J. Chem. Soc., Chem. Commun. 1992, 1186.
19. (c) Hale, K. J.; Delisser, V. M.; Manaviazar, S. Tetrahedron Lett. 1992, 33, 7613.
20. (d) Hale, K. J.; Cai, J.; Delisser, V.; Manaviazar, S.; Peak, S. A.; Bhatia, G. S.; Collins, T. C.; Jogiya, N. Tetrahedron 1996, 52, 1047.
21. (e) Depew, K. M.; Kamenecka, T. M.; Danishefsky, S. J. Tetrahedron Lett. 2000, 41, 289.
22. (a) Kumarn, S.; Shaw, D. M.; Longbottom, D. A.; Ley, S. V. Org. Lett. 2005, 7, 4189.
23. (b) Kumarn, S.; Shaw, D. M.; Ley, S. V. Chem. Commun. 2006, 3211.
24. For the α-amination of aldehydes, see: (a) Bøgevig, A.; Juhl, K.; Kumaragurubaran, N.; Zhuang, W.; Jørgensen, K. A. Angew. Chem. Int. Ed. 2002, 41, 1790.
25. (b) List, B. J. Am. Chem. Soc. 2002, 124, 5656.
26. (c) Vogt, H.; Vanderheiden, S.; Brase, S. Chem. Commun. 2003, 2448.
27. For α-amination on other substrates or its use in total synthesis, see: (d) Kumaragurubaran, N.; Juhl, K.; Zhuang, W.; Bøgevig, A.; Jørgensen, K. A. J. Am. Chem. Soc. 2002, 124, 6254.
28. (e) Juhl, K.; Jørgensen, K. A. J. Am. Chem. Soc. 2002, 124, 2420.
29. (f) Marigo, M.; Juhl, K.; Jørgensen, K. A. Angew. Chem. Int. Ed. 2003, 42, 1367.
30. (g) Saaby, S.; Bella, M.; Jørgensen, K. A. J. Am. Chem. Soc. 2004, 126, 8120.
31. (h) Pei, W.; Wei, H.-X.; Chen, D.; Headley, A. D.; Li, G. J. Org. Chem. 2003, 68, 8404.
32. (i) Iwamura, H.; Mathew, S. P.; Blackmond, D. G. J. Am. Chem. Soc. 2004, 126, 11770.
33. (j) Liu, X.; Li, H.; Deng, L. Org. Lett. 2005, 7, 167.
34. (k) Chowdari, N. S.; Barbas, C. F. III Org. Lett. 2005, 7, 867.
35. (l) Suri, J. T.; Steiner, D. D.; Barbas, C. F. III Org. Lett. 2005, 7, 3885.
36. Schweizer, E. E.; Hayes, J. E.; Hanawalt, E. M. J. Org. Chem. 1985, 50, 2591.
37. (a) Cobb, A. J. A.; Shaw, D. M.; Ley, S. V. Synlett 2004, 558.
38. (b) Cobb, A. J. A.; Longbottom, D. A.; Shaw, D. M.; Ley, S. V. Chem. Commun. 2004, 1808.
39. (c) Cobb, A. J. A.; Shaw, D. M.; Longbottom, D. A.; Gold, J. B.; Ley, S. V. Org. Biomol. Chem. 2005, 3, 84.
40. (d) Mitchell, C. E. T.; Brenner, S. E.; Ley, S. V. Chem. Commun. 2005, 5346.
41. (e) Knudsen, K. R.; Mitchell, C. E. T.; Ley, S. V. Chem. Commun. 2006, 66.
42. (f) Mitchell, C. E. T.; Brenner, S. E.; García-Fortanet, J.; Ley, S. V. Org. Biomol. Chem. 2006, 4, 2039.
43. (g) Franckevičius, V.; Knudsen, K. R.; Ladlow, M.; Longbottom, D. A.; Ley, S. V. Synlett 2006, 889.
44. (a) Torii, H.; Nakadai, M.; Ishihara, K.; Saito, S.; Yamamoto, H. Angew. Chem. Int. Ed. 2004, 43, 1983.
45. (b) Yamamoto, Y.; Momiyama, N.; Yamamoto, H. J. Am. Chem. Soc. 2004, 126, 5962.
46. (c) Momiyama, N.; Torii, H.; Saito, S.; Yamamoto, H. Proc. Nat. Acad. Sci. U.S.A. 2004, 101, 5374.
47. (a) Hartikka, A.; Arvidsson, P. I. Tetrahedron: Asymmetry 2004, 15, 1831.
48. (b) Hartikka, A.; Arvidsson, P. I. Eur. J. Org. Chem. 2005, 4287.
49. 4. Evaporation of the solvent gave the crude product, which was purified by flash column chromatography (PE-EtOAc = 9:1).
50. 4: 269.1501; found: 269.1495.
51. 4Na: 349.2103; found: 349.2112.
52. 4Na: 417.1790; found: 417.1776.