High-pressure-promoted asymmetric aldol reactions of ketones with aldehydes catalyzed by L-proline

Synlett

Volumn , Issue 11, 2003, Pages 1655-1658

  Sekiguchi, Yusuke ^a   Sasaoka, Aika ^a   Shimomoto, Ai ^a   Fujioka, Shingo ^a   Kotsuki, Hiyoshizo ^a  

^a KOCHI UNIVERSITY   (Japan)

Author keywords

Aldehydes; Asymmetric aldol reaction; High pressure; Ketones; L proline

Indexed keywords

ALDEHYDE; KETONE; PROLINE;

ALDOL REACTION; ARTICLE; CATALYSIS; HYPERBARISM;

EID: 0042912970     PISSN: 09365214     EISSN: None     Source Type: Journal    
DOI: 10.1055/s-2003-41424     Document Type: Article

References (54)

1. High-Pressure Organic Chemistry. Part 26. For Part 25, see: Kumamoto, K. ; Misawa, Y.; Tokita, S.; Kubo, Y.; Kotsuki, H. Tetrahedron Lett. 2002, 43, 1035.
2. (a) Heathcock, C. H. Comprehensive Organic Synthesis, Vol. 2; Trost, B. M.; Fleming, I.; Heathcock, C. H., Eds.; Pergamon Press: Oxford, 1991, Chap. 1.5.
3. (b) Mukaiyama, T.; Kobayashi, S. Org. React. 1994, 46, 1.
4. (a) Takayama, S.; McGarvey, G.; Wong, C.-H. Chem. Soc. Rev. 1997, 26, 407.
5. (b) Cowden, C. J.; Paterson, I. Org. React. 1997, 51, 1.
6. (c) Nelson, S. G. Tetrahedron: Asymmetry 1998, 9, 357.
7. (d) Gröger, H.; Vogl, E. M.; Shibasaki, M. Chem.-Eur. J. 1998, 4, 1137.
8. (e) Carreira, E. M. Comprehensive Asymmetric Synthesis, Vol. 3; Jacobsen, E. N.; Pfaltz, A.; Yamamoto, H., Eds.; Springer-Verlag: Berlin, 1999, Chap. 29.1.
9. (f) Machajewski, T. D.; Wong, C.-H. Angew. Chem. Int. Ed. 2000, 39, 1352.
10. (a) Gröger, H.; Wilken, J. Angew. Chem. Int. Ed. 2001, 40, 529.
11. (b) Dalko, P. I.; Moisan, L. Angew. Chem. Int. Ed. 2001, 40, 3726.
12. (c) List, B. Synlett 2001, 1675.
13. (d) Palomo, C.; Oiarbide, M.; García, J. M. Chem.-Eur. J. 2002, 8, 36.
14. (e) Alcaide, B.; Almendros, P. Eur. J. Org. Chem. 2002, 1595.
15. (f) Jarvo, E. R.; Miller, S. J. Tetrahedron 2002, 58, 2481.
16. (g) List, B. Tetrahedron 2002, 58, 5573.
17. (h) Alcaide, B.; Almendros, P. Angew. Chem. Int. Ed. 2003, 42, 858.
18. (i) Duthaler, R. O. Angew. Chem. Int. Ed. 2003, 42, 975.
19. (a) List, B.; Lerner, R. A.; Barbas, C. F. III J. Am. Chem. Soc. 2000, 122, 2395.
20. (b) Notz, W.; List, B. J. Am. Chem. Soc. 2000, 122, 7386.
21. (c) List, B.; Pojarliev, P.; Castello, C. Org. Lett. 2001, 3, 573.
22. (d) Pidathala, C.; Hoang, L.; Vignola, N.; List, B. Angew. Chem. Int. Ed. 2003, 42, 2785.
23. (a) Sakthivel, K.; Notz, W.; Bui, T.; Barbas, C. F. III J. Am. Chem. Soc. 2001, 123, 5260.
24. (b) Chowdari, N. S.; Ramachary, D. B.; Córdova, A.; Barbas, C. F. III Tetrahedron Lett. 2002, 43, 9591.
25. (c) Córdova, A.; Notz, W.; Barbas, C. F. III Chem. Commun. 2002, 3024.
26. (d) Chowdari, N. S.; Ramachary, D. B.; Barbas, C. F. III Org. Lett. 2003, 5, 1685.
27. For other examples of asymmetric aldol reactions under proline catalysis, see: (a) Bøgevig, A.; Kumaragurubaran, N.; Jørgensen, K. A. Chem. Commun. 2002, 620. (b) Northrup, A. B.; MacMillan, D. W. C. J. Am. Chem. Soc. 2002, 124, 6798. (c) Darbre, T.; Machuqueiro, M. Chem. Commun. 2003, 1090. (d) Tang, Z.; Jiang, F.; Yu, L.-T.; Cui, X.; Gong, L.-Z.; Mi, A.-Q.; Jiang, Y.-Z.; Wu, Y.-D. J. Am. Chem. Soc. 2003, 125, 5262. (e) See also: Nakadai, M.; Saito, S.; Yamamoto, H. Tetrahedron 2002, 58, 8167; and references cited therein.
28. For other examples of asymmetric aldol reactions under proline catalysis, see: (a) Bøgevig, A.; Kumaragurubaran, N.; Jørgensen, K. A. Chem. Commun. 2002, 620. (b) Northrup, A. B.; MacMillan, D. W. C. J. Am. Chem. Soc. 2002, 124, 6798. (c) Darbre, T.; Machuqueiro, M. Chem. Commun. 2003, 1090. (d) Tang, Z.; Jiang, F.; Yu, L.-T.; Cui, X.; Gong, L.-Z.; Mi, A.-Q.; Jiang, Y.-Z.; Wu, Y.-D. J. Am. Chem. Soc. 2003, 125, 5262. (e) See also: Nakadai, M.; Saito, S.; Yamamoto, H. Tetrahedron 2002, 58, 8167; and references cited therein.
29. For other examples of asymmetric aldol reactions under proline catalysis, see: (a) Bøgevig, A.; Kumaragurubaran, N.; Jørgensen, K. A. Chem. Commun. 2002, 620. (b) Northrup, A. B.; MacMillan, D. W. C. J. Am. Chem. Soc. 2002, 124, 6798. (c) Darbre, T.; Machuqueiro, M. Chem. Commun. 2003, 1090. (d) Tang, Z.; Jiang, F.; Yu, L.-T.; Cui, X.; Gong, L.-Z.; Mi, A.-Q.; Jiang, Y.-Z.; Wu, Y.-D. J. Am. Chem. Soc. 2003, 125, 5262. (e) See also: Nakadai, M.; Saito, S.; Yamamoto, H. Tetrahedron 2002, 58, 8167; and references cited therein.
30. For other examples of asymmetric aldol reactions under proline catalysis, see: (a) Bøgevig, A.; Kumaragurubaran, N.; Jørgensen, K. A. Chem. Commun. 2002, 620. (b) Northrup, A. B.; MacMillan, D. W. C. J. Am. Chem. Soc. 2002, 124, 6798. (c) Darbre, T.; Machuqueiro, M. Chem. Commun. 2003, 1090. (d) Tang, Z.; Jiang, F.; Yu, L.-T.; Cui, X.; Gong, L.-Z.; Mi, A.-Q.; Jiang, Y.-Z.; Wu, Y.-D. J. Am. Chem. Soc. 2003, 125, 5262. (e) See also: Nakadai, M.; Saito, S.; Yamamoto, H. Tetrahedron 2002, 58, 8167; and references cited therein.
31. For other examples of asymmetric aldol reactions under proline catalysis, see: (a) Bøgevig, A.; Kumaragurubaran, N.; Jørgensen, K. A. Chem. Commun. 2002, 620. (b) Northrup, A. B.; MacMillan, D. W. C. J. Am. Chem. Soc. 2002, 124, 6798. (c) Darbre, T.; Machuqueiro, M. Chem. Commun. 2003, 1090. (d) Tang, Z.; Jiang, F.; Yu, L.-T.; Cui, X.; Gong, L.-Z.; Mi, A.-Q.; Jiang, Y.-Z.; Wu, Y.-D. J. Am. Chem. Soc. 2003, 125, 5262. (e) See also: Nakadai, M.; Saito, S.; Yamamoto, H.Tetrahedron 2002, 58, 8167; and references cited therein.
32. For the same reason, ionic liquids were introduced as novel reaction media: (a) Loh, T.-P.; Feng, L.-C.; Yang, H.-Y.; Yang, J.-Y. Tetrahedron Lett. 2002, 43, 8741. (b) Kotrusz, P.; Kmentová, I.; Gotov, B.; Toma, S.; Solcániová, E. Chem. Commun. 2002, 2510. (c) See also: Peng, Y.-Y.; Ding, Q.-P.; Li, Z.; Wang, P. G.; Cheng, J.-P. Tetrahedron Lett. 2003, 44, 3871.
33. For the same reason, ionic liquids were introduced as novel reaction media: (a) Loh, T.-P.; Feng, L.-C.; Yang, H.-Y.; Yang, J.-Y. Tetrahedron Lett. 2002, 43, 8741. (b) Kotrusz, P.; Kmentová, I.; Gotov, B.; Toma, S.; Solcániová, E. Chem. Commun. 2002, 2510. (c) See also: Peng, Y.-Y.; Ding, Q.-P.; Li, Z.; Wang, P. G.; Cheng, J.-P. Tetrahedron Lett. 2003, 44, 3871.
34. For the same reason, ionic liquids were introduced as novel reaction media: (a) Loh, T.-P.; Feng, L.-C.; Yang, H.-Y.; Yang, J.-Y. Tetrahedron Lett. 2002, 43, 8741. (b) Kotrusz, P.; Kmentová, I.; Gotov, B.; Toma, S.; Solcániová, E. Chem. Commun. 2002, 2510. (c) See also: Peng, Y.-Y.; Ding, Q.-P.; Li, Z.; Wang, P. G.; Cheng, J.-P. Tetrahedron Lett. 2003, 44, 3871.
35. For a recent review, see: Jenner, G. Tetrahedron 2002, 58, 5185.
36. For some recent examples of high-pressure-promoted aldol and related reactions, see: (a) Desmaële, D. Tetrahedron Lett. 1996, 37, 1233. (b) Bellassoued, M.; Reboul, E.; Dumas, F. Tetrahedron Lett. 1997, 38, 5631. (c) Jenner, G. New J. Chem. 1999, 23, 525. (d) Jenner, G. Tetrahedron Lett. 2001, 42, 243. (e) Misumi, Y.; Bulman, R. A.; Matsumoto, K. Heterocycles 2002, 56, 599. (f) Misumi, Y.; Matsumoto, K. Angew. Chem. Int. Ed. 2002, 41, 1031.
37. For some recent examples of high-pressure-promoted aldol and related reactions, see: (a) Desmaële, D. Tetrahedron Lett. 1996, 37, 1233. (b) Bellassoued, M.; Reboul, E.; Dumas, F. Tetrahedron Lett. 1997, 38, 5631. (c) Jenner, G. New J. Chem. 1999, 23, 525. (d) Jenner, G. Tetrahedron Lett. 2001, 42, 243. (e) Misumi, Y.; Bulman, R. A.; Matsumoto, K. Heterocycles 2002, 56, 599. (f) Misumi, Y.; Matsumoto, K. Angew. Chem. Int. Ed. 2002, 41, 1031.
38. For some recent examples of high-pressure-promoted aldol and related reactions, see: (a) Desmaële, D. Tetrahedron Lett. 1996, 37, 1233. (b) Bellassoued, M.; Reboul, E.; Dumas, F. Tetrahedron Lett. 1997, 38, 5631. (c) Jenner, G. New J. Chem. 1999, 23, 525. (d) Jenner, G. Tetrahedron Lett. 2001, 42, 243. (e) Misumi, Y.; Bulman, R. A.; Matsumoto, K. Heterocycles 2002, 56, 599. (f) Misumi, Y.; Matsumoto, K. Angew. Chem. Int. Ed. 2002, 41, 1031.
39. For some recent examples of high-pressure-promoted aldol and related reactions, see: (a) Desmaële, D. Tetrahedron Lett. 1996, 37, 1233. (b) Bellassoued, M.; Reboul, E.; Dumas, F. Tetrahedron Lett. 1997, 38, 5631. (c) Jenner, G. New J. Chem. 1999, 23, 525. (d) Jenner, G. Tetrahedron Lett. 2001, 42, 243. (e) Misumi, Y.; Bulman, R. A.; Matsumoto, K. Heterocycles 2002, 56, 599. (f) Misumi, Y.; Matsumoto, K. Angew. Chem. Int. Ed. 2002, 41, 1031.
40. For some recent examples of high-pressure-promoted aldol and related reactions, see: (a) Desmaële, D. Tetrahedron Lett. 1996, 37, 1233. (b) Bellassoued, M.; Reboul, E.; Dumas, F. Tetrahedron Lett. 1997, 38, 5631. (c) Jenner, G. New J. Chem. 1999, 23, 525. (d) Jenner, G. Tetrahedron Lett. 2001, 42, 243. (e) Misumi, Y.; Bulman, R. A.; Matsumoto, K. Heterocycles 2002, 56, 599. (f) Misumi, Y.; Matsumoto, K. Angew. Chem. Int. Ed. 2002, 41, 1031.
41. For some recent examples of high-pressure-promoted aldol and related reactions, see: (a) Desmaële, D. Tetrahedron Lett. 1996, 37, 1233. (b) Bellassoued, M.; Reboul, E.; Dumas, F. Tetrahedron Lett. 1997, 38, 5631. (c) Jenner, G. New J. Chem. 1999, 23, 525. (d) Jenner, G. Tetrahedron Lett. 2001, 42, 243. (e) Misumi, Y.; Bulman, R. A.; Matsumoto, K. Heterocycles 2002, 56, 599. (f) Misumi, Y.; Matsumoto, K. Angew. Chem. Int. Ed. 2002, 41, 1031.
42. 2. The crude product was purified by preparative TLC (hexane/EtOAc = 2:1) to afford the desired adduct (74 mg, 90%). The ee value was determined by HPLC analysis using a Daicel Chiralpak AD column, with 1% 2-propanol in hexane as the eluent, at 0.5 mL/min.
43. Bordwell, F. G.; Zhang, X.-M. Acc. Chem. Res. 1993, 26, 510.
44. (a) Bahmanyar, S.; Houk, K. N. J. Am. Chem. Soc. 2001, 123, 11273.
45. (b) Bahmanyar, S.; Houk, K. N. J. Am. Chem. Soc. 2001, 123, 12911.
46. (c) Hoang, L.; Bahmanyar, S.; Houk, K. N.; List, B. J. Am. Chem. Soc. 2003, 125, 16.
47. (d) Bahmanyar, S.; Houk, K. N. Org. Lett. 2003, 5, 1249.
48. (e) Bahmanyar, S.; Houk, K. N.; Martin, H. J.; List, B. J. Am. Chem. Soc. 2003, 125, 2475.
49. (f) See also: Arnó, M.; Domingo, L. R. Theor. Chem. Acc. 2002, 108, 232.
50. (g) Rankin, K. N.; Gauld, J. W.; Boyd, R. J. J. Phys. Chem. A 2002, 106, 5155.
51. (a) Sera, A.; Takagi, K.; Katayama, H.; Yamada, H.; Matsumoto, K. J. Org. Chem. 1988, 53, 1157.
52. (b) Oishi, T.; Oguri, H.; Hirama, M. Tetrahedron: Asymmetry 1995, 6, 1241.
53. (c) Markó, I. E.; Giles, P. R.; Hindley, N. J. Tetrahedron 1997, 53, 1015.
54. 5a,6a this type of asymmetric catalysis is best performed in dry DMSO.