Direct catalytic asymmetric Mannich reaction of unmodified ketones: Cooperative catalysis of an AlLibis(binaphthoxide) complex and La(OTf)3·nH2O

Tetrahedron

Volumn 55, Issue 29, 1999, Pages 8857-8867

  Yamasaki, Shingo ^a   Iida, Takehiko ^a   Shibasaki, Masakatsu ^a  

^a UNIVERSITY OF TOKYO   (Japan)

Author keywords

[No Author keywords available]

Indexed keywords

3 (DIETHYLAMINO) 2 METHYL 1 PHENYL 1 PROPANONE; KETONE DERIVATIVE; UNCLASSIFIED DRUG;

ALKYLATION; CATALYSIS; COMPLEX FORMATION; CONFERENCE PAPER; DRUG SYNTHESIS; ENANTIOMER; INFRARED SPECTROMETRY; METHYLATION; PRIORITY JOURNAL; REACTION ANALYSIS;

EID: 0033575409     PISSN: 00404020     EISSN: None     Source Type: Journal    
DOI: 10.1016/S0040-4020(99)00449-4     Document Type: Conference Paper

References (38)

1. For an excellent review of Mannich reactions, see; Arend, M; Westermann, B.; Risch, N. Angew. Chem. Int. Ed. 1998, 37, 1044-1070.
2. Traxler, P; Trinks, U.; Buchdunger, E.; Mett, H.; Meyer, T.; Müller, M.; Regenass, U.; Rösel, J.; Lydon, N. J. Med. Chem. 1995, 38, 2441-2448 and references cited therein.
3. a) Corey, E. J.; Decicco, C. P.; Newbold, R. C. Tetrahedron Lett. 1991, 39, 5287-5290;
4. b) Ishihara, K.; Miyata, M.; Hattori, K.; Tada, T.; Yamamoto, H. J. Am. Chem. Soc. 1994, 116, 10520-10524;
5. c) Enders, D.; Ward, D.; Adam, J.; Raabe, G. Angew. Chem. Int. Ed. 1996, 35, 981-984.
6. Fujieda, H.; Kanai, M.; Kambara, T.; Iida, A.; Tomioka, K. J. Am. Chem. Soc. 1997, 119, 2060-2061.
7. a) Ishitani, H.; Ueno, M.; Kobayashi, S. J. Am. Chem. Soc. 1997, 119, 7153-7154;
8. b) Kobayashi, S.; Ishitani, H.; Ueno, M. J. Am. Chem. Soc. 1998, 120, 431-432.
9. Hagiwara, E.; Fujii, A.; Sodeoka, M. J. Am. Chem. Soc. 1998, 120, 2474-2475.
10. Ferraris, D.; Young, B.; Dudding, T.; Lectka, T. J. Am. Chem. Soc. 1998, 120, 4548-4549.
11. Yamasaki, S.; Iida, T.; Shibasaki, M. Tetrahedron Lett. 1999, 40, 307-310.
12. For a review of the heterobimetallic asymmetric catalysts, see; Shibasaki, M.; Sasai, H.; Arai, T. Angew. Chem. Int. Ed. 1997, 36, 1236-1256.
13. a) Yamada, Y. M. A.; Yoshikawa, N.; Sasai, H.; Shibasaki, M. Angew. Chem. Int. Ed. 1997, 36, 1871-1873;
14. b) Gröger, H.; Vogl, E. M.; Shibasaki, M. Chem. Eur. J. 1998, 4, 1137-1141. Recently we developed a direct catalytic asymmetric aldol reactions promoted by a novel barium complex, see: Yamada, Y. M. A.; Shibasaki, M. Tetrahedron Lett. 1998, 39, 5561-5564.
15. b) Gröger, H.; Vogl, E. M.; Shibasaki, M. Chem. Eur. J. 1998, 4, 1137-1141. Recently we developed a direct catalytic asymmetric aldol reactions promoted by a novel barium complex, see: Yamada, Y. M. A.; Shibasaki, M. Tetrahedron Lett. 1998, 39, 5561-5564.
16. a) Sasai, H.; Tokunaga, T.; Watanabe, S.; Suzuki, T.; Ito, N.; Shibasaki, M. J. Org. Chem. 1995, 60, 7388-7399 and references cited therein.
17. For other examples for catalytic asymmetric nitroaldol reactions using the hydrated LnLB (Ln = lanthanoid) complexes, see; b) Takaoka, E.; Yoshikawa, N.; Yamada Y. M. A.; Sasai H.; Shibasaki, M. Hetemcycles 1997, 46, 157-163;
18. c) Sasai H.; Hiroi M.; Yamada Y. M. A.; Shibasaki M. Tetrahedron Lett. 1997, 38, 6031-6034.
19. Yamazaki, M.; Aoki, Y.; Kato, H.; Ito, Y.; Kontani, H.; Koshiura, R. Yakugaku Zasshi 1987, 107, 705-710.
20. The reaction in THF afforded 4 with lower ee than that in toluene.
21. Stewert, T. D.; Bradly, W. E. J. Am. Chem. Soc. 1932, 54, 4172-4183.
22. 4, and following separation of the resultant diastereomers.
23. Arai, T; Sasai, H.; Aoe, K.; Okamura, K.; Date, T.; Shibasaki, M. Angew. Chem. Int. Ed. 1996, 35, 104-106.
24. a) Arai, T.; Bougauchi, M.; Sasai, H.; Shibasaki, M. J. Org. Chem. 1996, 61, 2926-2927;
25. b) Keller, E.; Veldman, N.; Spek, A. L.; Feringa, B. L. Tetrahedron: Asymmetry 1997, 8, 3403-3408;
26. c) Arai, T.; Sasai, H.; Yamaguchi, K.; Shibasaki, M. J. Am. Chem. Soc. 1998, 120, 441-442;
27. d) Yamada, K.; Arai, T.; Sasai, H.; Shibasaki, M. J. Org. Chem. 1998, 63, 3666-3672;
28. e) Shimizu, S.; Ohori, K.; Arai, T.; Sasai, H.; Shibasaki, M. J. Org. Chem. 1998, 63, 7547-7551.
29. a)Hanson, R. M.; Sharpless, K. B. J. Org. Chem. 1986, 51, 1922-1925;
30. b) Narasaka, K.; Iwasawa, N.; Inoue, M. Yamada, T.; Nakashima, M. Sugimori, J. J. Am. Chem. Soc. 1989, 111, 5340-5345;
31. c) Mikami, K.;Terada, M. Nakai, T. J. Am. Chem. Soc. 1990, 112, 3949-3954;
32. d) Terada, M. Matsumoto, Y.;Nakamura, Y.;Mokami, K. Chem. Commun. 1997, 281-282;
33. d) Bougauchi M.; Watanabe, S.; Arai, T.; Sasai, H.; Shibasaki, M. J. Am. Chem. Soc. 1997, 119, 2329-2330;
34. e) Iida, T.; Yamamoto, N.; Sasai, H.; Shibasaki, M. J. Am.chem. Soc. 1997, 119, 4783-4784;
35. f) Iida, T. Yamamolo, N.; Matsunaga, S.; Woo, H.-G.; Shibasaki, M. Angew. Chem. Int. Ed. 1998, 2223-2226.
36. Although the absolute configurations of 11-13 have not been determined at the present time, we suggest (S)-configuration similar to compound 14 because of analogies of their molecular modeling studies for the transition state.
37. All of those Mannich bases showed a tendency to racemize during colomn choromatograpy (silica gel or alumina).
38. Mosher, H. S. J. Am. Chem. Soc. 1973, 95, 512-519.