Hetero-Diels-Alder reactions of ketones - A challenge for chemists

European Journal of Organic Chemistry

Volumn , Issue 10, 2004, Pages 2093-2102

  Jørgensen, Karl Anker ^a  

^a AARHUS UNIVERSITY   (Denmark)

Author keywords

Alkenes; Asymmetric catalysis; Cycloaddition; Ketones; Synthesis design

Indexed keywords

AMINE; CARBOHYDRATE; COPPER; ESTER DERIVATIVE; KETONE DERIVATIVE; LACTONE DERIVATIVE; LEWIS ACID; ZINC;

CATALYSIS; CHEMICAL REACTION; CHEMISTRY; CHIRALITY; ENANTIOSELECTIVITY; HYDROGEN BOND; SHORT SURVEY; SYNTHESIS;

EID: 4544247886     PISSN: 1434193X     EISSN: None     Source Type: Journal    
DOI: 10.1002/ejoc.200300766     Document Type: Short Survey

References (53)

1. See, for example: [1a] L. F. Tietze, G. Kettschau, Top. Curr. Chem. 1997, 189, 1 and references therein.
2. [1b] D. L. Boger, S. M. Weinreb, Hetero-Diels-Alder Methodology in Organic Synthesis (Ed.: H. H. Wasserman), Academic Press: San Diego, CA, 1987.
3. See, for example: [2a] A. Kumar, Chem. Rev. 2001, 101, 1.
4. [2b] K. A. Jørgensen, Angew. Chem. Int. Ed. 2001, 39, 3558.
5. For recent reviews on asymmetric synthesis of quaternary carbon centers see: [3a] M. Cristoffers, A. Mann, Angew. Chem. Int. Ed. 2001, 40, 4591.
6. [3b] E. J. Corey, A. Guzman-Perez, Angew. Chem. Int. Ed. 1998, 37, 388.
7. F.-G. Klärner, F. Wurche, J. Prakt. Chem. 2000, 342, 609.
8. Y. Huang, V. H. Rawal, J. Am. Chem. Soc. 2002, 124, 9662.
9. L. R. Dominge, J. Andrés, J. Org. Chem. 2003, 68, 8662.
10. Y. Huand, A. K. Unni, A. N. Thadani, V. H. Rawal, Nature 2003, 403, 146.
11. C. Pierres, P. George, L. Van Hijfte, J.-B. Ducep, M. Hilbert, A. Mann, Tetrahedron Lett. 2003, 44, 3645.
12. M. N. Milland, R. S. Graham, J. Am. Chem. Soc. 1984, 106, 4294.
13. Y. Huang, V. H. Rawal, Org. Lett. 2000, 2, 3321.
14. For recent reviews dealing with chiral bis(oxazoline)-Lewis acid complexes as catalysts see, for example. [11a] A. K. Ghosh, P. Mathivanen, J. Cappiello, Tetrahedron: Asymmetry 1998, 9, 1.
15. [11b] K. A. Jørgensen, M. Johannsen, S. Yao, H. Audrain, J. Thorhauge, Acc. Chem. Res. 1999, 32, 605.
16. [11c] J. S. Johnson, D. A. Evans, Acc. Chem. Res. 2000, 33, 325.
17. [12a] M. Johannsen, S. Yao, K. A. Jørgensen, Chem. Commun. 1997, 2169.
18. [12b] M. Johannsen, S. Yao, H. Audrian, R. G. Hazell, K. A. Jørgensen, J. Am. Chem. Soc. 1998, 120, 8599; see also: M. Quimpére, K. Jankowski, J. Chem. Soc., Chem. Commun. 1987, 676.
19. [12b] M. Johannsen, S. Yao, H. Audrian, R. G. Hazell, K. A. Jørgensen, J. Am. Chem. Soc. 1998, 120, 8599; see also: M. Quimpére, K. Jankowski, J. Chem. Soc., Chem. Commun. 1987, 676.
20. P. I. Dalko, L. Moisan, J. Cossy, Angew. Chem. Int. Ed. 2002, 41, 625.
21. S. Yao, M. Roberson, F. Reichel, R. G. Hazell, K. A. Jørgensen, J. Org. Chem. 1999, 64, 6677.
22. C. Bolm, O. Simic, J. Am. Chem. Soc. 2001, 123, 3830.
23. C. Bolm, M. Verrucci, A. Simic, P. G. Cossi, G. Rabe, H. Okamura, Chem. Commun. 2003, 2816.
24. H. Furuno, T. Kamabara, Y. Tanaka, T. Hanamoto, T. Kagawa, J. Inanaga, Tetrahedron Lett. 2003, 44, 6129.
25. [18a] L. F. Tietze, P. Salling, Synlett 1992, 281.
26. [18b] L. F. Tietze, P. Salling, Chirality 1993, 5, 329.
27. For Lewis acid catalyzed: [19a] E. Wada, S. Kanemasa, O. Tsuge, Chem. Lett. 1989, 675.
28. [19b] E. Wada, H. Yasuoka, S. Kanemasa, Chem. Lett. 1994, 145.
29. For chiral Lewis-acid catalyzed: [19c] E. Wada, H. Yasuoka, S. Kanemasa, Chem. Lett. 1994, 1637.
30. [19d] E. Wada, W. Pei, H. Yasuoka, S. Kanemasa, Tetrahedron 1996, 52, 1205.
31. [20a] D. A. Evans, J. S. Johnson, J. Am. Chem. Soc. 1998, 120, 4895.
32. [20b] D. A. Evans, E. J. Olhava, J. S. Johnson, J. M. Janey, Angew. Chem. Int. Ed. 1998, 37, 3372.
33. [20c] D. A. Evans, J. S. Johnson, C. S. Burgy, K. R. Campos, Tetrahedron Lett. 1999, 40, 2879.
34. [20d] D. A. Evans, J. S. Johnson, E. J. Olhava, J. Am. Chem. Soc. 2000, 122, 1635.
35. J. Thorhauge, M. Johannsen, K. A. Jørgensen, Angew. Chem. Int. Ed. 1998, 37, 2404.
36. H. Audrian, J. Thorhauge, R. G. Hazell, K. A. Jørgensen, J. Org. Chem. 2000, 65, 4487.
37. [23a] F. Perron, K. F. Albizati, Chem. Rev. 1989, 89, 1617.
38. [23b] A. Bertolozzi, G. Capozzi, C. Falciani, S. Menichetti, C. Naitvi, A. P. Bacialli, J. Org. Chem. 1999, 64, 6490.
39. W. Zhuang, J. Thorhauge, K. A. Jørgensen, Chem. Commun. 2000, 459.
40. See, for example: [25a] A. E. Stütz, Imino sugars as Glycosidases Inhibitors; Nojirimycin and beyond, Wiley-VCH Verlag, Weinheim 1999.
41. [25b] S. P. Clissold, C. Edwards, Drugs 1988, 35, 214.
42. [25c] J. A. Balfour, D. McTavish, Drugs 1993, 46, 1025.
43. [25d] D. P. Calfee, F. G. Heyden, Drugs 1998, 58, 537.
44. J. Thorhauge, M. Roberson, R. G. Hazell, K. A. Jørgensen, Chem. Eur. J. 2000, 8, 1888.
45. H. Audrain, K. A. Jørgensen, J. Am. Chem. Soc. 2000, 122, 11543.
46. [28a] E. Wada, G. Kumaran, S. Kanamasa, Tetrahedron Lett. 2000, 41, 73.
47. [28b] E. Wada, H. Koga, G. Kumaran, Tetrahedron Lett. 2002, 43, 9397.
48. [28c] H. Koga, E. Wada, Tetrahedron Lett. 2003, 44, 715.
49. K. Gademann, D. E. Chavez, E. N. Jacobsen, Angew. Chem. Int. Ed. 2002, 41, 3059.
50. K. Juhl, K. A. Jørgensen, Angew. Chem. Int. Ed. 2003, 42, 1498.
51. G. Cravotto, G. M. Nano, G. Pakmisano, S. Tagliapietra, Tetrahedron: Asymmetry 2001, 12, 707.
52. For a recent one-step organocatalytic synthesis of optically active warfarin see: N. Halland, T. Hansen, K. A. Jørgensen, Angew. Chem. Int. Ed. 2003, 42, 4955.
53. L.-L. Wei, R. P. Hsung, H. Xiong, J. A. Mulder, N. T. Nksnsah, Org. Lett. 1999, 1, 2145.