L-proline-catalyzed one-pot three-component reaction for the synthesis of β-alkoxy ketones

Synthesis

Volumn , Issue 19, 2006, Pages 3238-3242

  Dodda, Rajasekhar ^a   Zhao, Cong Gui ^a  

^a UNIVERSITY OF TEXAS AT SAN ANTONIO   (United States)

Author keywords

alkoxy ketones; Alcohols; Aldehydes; Aldol reactions; Mannich addition; One pot reaction

Indexed keywords

ALCOHOLS; ALDEHYDES; CATALYST ACTIVITY; REACTION KINETICS; SUBSTITUTION REACTIONS; SYNTHESIS (CHEMICAL);

ALDOL REACTIONS; MANNICH ADDITION; ONE POT REACTION;

KETONES;

ALCOHOL DERIVATIVE; ALDEHYDE DERIVATIVE; BETA ALKOXY KETONE DERIVATIVE; KETONE DERIVATIVE; METHANOL; PROLINE; UNCLASSIFIED DRUG;

ARTICLE; CATALYSIS; CHEMICAL ANALYSIS; CHEMICAL REACTION; ENANTIOSELECTIVITY; SYNTHESIS;

EID: 33750034911     PISSN: 00397881     EISSN: None     Source Type: Journal    
DOI: 10.1055/s-2006-950184     Document Type: Article

References (39)

1. Kim, B. M.; Williams, S. F.; Masamune, S. In Comprehensive Organic Synthesis, Vol. 2; Trost, B. M.; Fleming, I.; Heathcock, C. H., Eds.; Pergamon: Oxford, 1991, 229-275.
2. (a) Mukaiyama, T.; Hayashi, M. Chem. Lett. 1974, 15.
3. (b) Mukaiyama, T. Angew. Chem., Int. Ed. Engl. 1977, 16, 817.
4. (c) Murata, S.; Suzuki, M.; Noyori, R. J. Am. Chem. Soc. 1980, 102, 3248.
5. (d) Noyori, R.; Murata, S.; Suzuki, M. Tetrahedron 1981, 37, 3899.
6. (e) Murata, S.; Suzuki, M.; Noyori, R. Tetrahedron 1988, 44, 4259.
7. (f) Ishitani, H.; Iwamoto, M. Tetrahedron Lett. 2003, 44, 299.
8. (g) Cossy, J.; Lutz, F.; Alauze, V.; Meyer, C. Synlett 2002, 45.
9. (h) Trehan, A.; Vij, A.; Walia, M.; Kaur, G.; Verma, R. D.; Trehan, S. Tetrahedron Lett. 1993, 34, 7335.
10. (i) Le Roux, C.; Ciliberti, L.; Laurent-Robert, H.; Laporterie, A.; Dubac, J. Synlett 1998, 1249.
11. (j) Ooi, T.; Tayama, E.; Takahashi, M.; Maruoka, K. Tetrahedron Lett. 1997, 38, 7043.
12. (k) Kamata, M.; Yokoyama, Y.; Karasawa, N.; Kato, M.; Hasegawa, E. Tetrahedron Lett. 1996, 37, 3483.
13. Kamata, M.; Nagai, S.; Kato, M.; Hasegawa, E. Tetrahedron Lett. 1996, 37, 7779.
14. (m) Mukaiyama, T.; Kobayashi, S.; Murakami, M. Chem. Lett. 1984, 1759.
15. (n) Mukaiyama, T.; Iwakiri, H. Chem. Lett. 1985, 1363.
16. (o) Murakami, M.; Minamikawa, H.; Mukaiyama, T. Chem. Lett. 1987, 1051.
17. (p) Sakurai, H.; Sasaki, K.; Hosomi, A. Bull. Chem. Soc. Jpn. 1983, 56, 3195.
18. (q) Hosomi, A.; Sakata, Y.; Sakurai, H. Chem. Lett. 1983, 405.
19. (r) Jung, M. E.; Hogan, K. T. Tetrahedron Lett. 1988, 29, 6199.
20. (s) Kawai, M.; Onaka, M.; Izumi, Y. Bull. Chem. Soc. Jpn. 1988, 61, 1237.
21. (a) Li, L.-S.; Das, S.; Sinha, S. C. Org. Lett. 2004, 6, 127.
22. (b) Silvermann, I. T.; Edington, C.; Elloitt, J. D.; Johnson, W. S. J. Org. Chem. 1987, 52, 180.
23. Cullen, A. J.; Sammakia, T. Org. Lett. 2004, 6, 3143.
24. (a) Stewart, I. C.; Bergman, R. G.; Toste, F. D. J. Am. Chem. Soc. 2003, 125, 8696.
25. (b) Kisanga, P. B.; Ilankumaran, P.; Fetterly, B. M.; Verkade, J. G. J. Org. Chem. 2002, 67, 3555.
26. Miller, K. J.; Kitagawa, T. T.; Abu-Omar, M. M. Organometallics 2001, 20, 4403.
27. Kabashima, H.; Katou, T.; Hattorri, H. Appl. Catal., A 2001, 214, 121.
28. Suga, S.; Suzuki, S.; Yamamoto, A.; Yoshida, J.-I. J. Am. Chem. Soc. 2000, 122, 10244.
29. Masuyama, Y.; Kobayashi, Y.; Yanagi, R.; Kurusu, Y. Chem. Lett. 1992, 2039.
30. Samanta, S.; Liu, J.; Dodda, R.; Zhao, C.-G. Org. Lett. 2005, 7, 5321.
31. (a) Cordova, A.; Notz, W.; Barbas, C. F. III Chem. Commun. 2002, 3024.
32. (b) Darbre, T.; Machuqueiro, M. Chem. Commun. 2003, 1090.
33. (c) Wu, Y.-S.; Shao, W.-Y.; Zheng, C.-Q.; Huang, Z.-L.; Cai, J.; Deng, Q.-Y. Helv. Chim. Acta 2004, 87, 1377.
34. (d) Peng, Y.-Y.; Ding, Q.-P.; Li, Z.; Wang, P. G.; Cheng, J.-P. Tetrahedron Lett. 2003, 44, 3871.
35. (e) Samanta, S.; Dodda, R.; Zhao, C.-G. unpublished results.
36. (a) Torii, H.; Nakadai, M.; Ishihara, K.; Saito, S.; Yamamoto, H. Angew. Chem. Int. Ed. 2004, 43, 1983.
37. (b) Cobb, A. J. A.; Shaw, D. M.; Ley, S. V. Synlett 2004, 558.
38. List, B.; Lerner, R. A.; Barbas, C. F. III J. Am. Chem. Soc. 2000, 122, 2395.
39. List, B.; Pojarliev, P.; Castello, C. Org. Lett. 2001, 3, 573.