3-Aminopyrrolidine lithium amide in enantioselective: Addition of organolithium compounds onto aromatic aldehydes

Tetrahedron Asymmetry

Volumn 8, Issue 10, 1997, Pages 1519-1523

  Corruble, Aline ^a   Valnot, Jean Yves ^a   Maddaluno, Jacques ^a   Duhamel, Pierre ^a  

^a UNIVERSITÉ DE ROUEN   (France)

Author keywords

[No Author keywords available]

Indexed keywords

ALDEHYDE; ORGANOLITHIUM COMPOUND;

ARTICLE; CHIRALITY; DRUG SYNTHESIS; NUCLEAR MAGNETIC RESONANCE SPECTROSCOPY; PRIORITY JOURNAL; REACTION ANALYSIS; STEREOCHEMISTRY;

EID: 0030914706     PISSN: 09574166     EISSN: None     Source Type: Journal    
DOI: 10.1016/S0957-4166(97)00114-6     Document Type: Article

References (38)

1. Whitesell, J. K.; Bao-Rong, J. J. Org. Chem. 1981, 46, 2798.
2. Important contributions in the field: (a) Mukaiyama, T.; Soai, K.; Sato, T.; Shimizu, H.; Suzuki, K. J. Am. Chem. Soc. 1979, 101, 1455.
3. (b) Mazaleyrat, J. P.; Cram, D. J. J. Am. Chem. Soc. 1981, 103, 4585.
4. c) Eleveld, M. B.; Hogeveen, H. Tetrahedron Lett. 1984, 25, 5187.
5. d) Kanoh, S.; Muramoto, H.; Maeda, K.; Kawaguchi, N.; Motoi, M.; Suda, H. Bull. Chem. Soc. Jpn. 1988, 61, 2244.
6. (e) Ye, M.; Logaraj, S.; Jackman, L. M.; Hillegrass, K.; Hirsh, K. A.; Bollinger, A. M.; Grosz, A. L. Tetrahedron 1994, 50, 6109.
7. f) Basu, A.; Beak, P. J. Am. Chem. Soc. 1996, 118, 1575. Reviews:
8. g) Solladié, G., Asymmetric Synthesis; Vol. 2; Morisson, J. D., Scott, J. W. Eds.; Academic Press: Orlando, 1983; pp. 157.
9. h) Tomioka, K. Synthesis 1990, 541.
10. i) Noyori, R. Asymmetric catalysis in organic synthesis; John Wiley and sons: New York, 1994; p. 255.
11. a) Whitesell, J. K.; Felman, S. W. J. Org. Chem. 1980, 45, 755.
12. b) Duhamel, L.; Plaquevent, J.-C. Tetrahedron Lett. 1980, 21, 2521.
13. 13C NMR study has been undertaken to check this point: Corruble, A.; Valnot, J. Y.; Maddaluno, J.; Prigent, Y.; Davoust, D.; Duhamel, P. submitted.
14. Hilmersson, G.; Davidsson, Ö. J. Organomet. Chem. 1995, 489, 175.
15. See for instance: Bowers-Nemia, M. M.; Lee J.; Joullié, M. M. Synth. Comm. 1983, 13, 1117.
16. (b) Bath, K. L.; Flanagan, B. M.; Joullié, M. M. Synth. Comm. 1985, 15, 587.
17. (c) Rosen, T.; Chu, D. T. W.; Lico, I. M.; Fernandes, P. B., Shen, L.; Borodkin S.; Pernet, A. G. J. Med. Chem. 1988, 31, 1586.
18. (d) Barco, A.; Benetti, S.; Casolari, A.; Pollini G. P.; Spalluto, G. Tetrahedron Lett. 1990, 31, 3039.
19. (e) Rapoport, H.; Williams, M. A. J. Org. Chem. 1994, 59, 3616.
20. (f) Andres, C. J.; Lee, P. H.; Nguyen, T. H.; Meyers, A. I. J. Org. Chem. 1995, 60, 3189.
21. (g) Tomori, H.; Shibutani, K.; Ogura, K. Heterocycles 1997, 44, 213.
22. Mukaiyama, T.; Asami, M. Top. Curr. Chem. 1985, 127, 133.
23. Maddaluno, J.; Corruble, A.; Leroux, V.; Plé, G.; Duhamel, P. Tetrahedron: Asymm. 1992, 3, 1239.
24. O'Donnell, M. J.; Polt, R. B. J. Org. Chem. 1982, 2663.
25. (a) Hamman, S.; Barelle, M.; Tetaz, F.; Beguin, C. G. J. Fluorine Chem. 1987, 37, 85.
26. (b) Takeuchi, Y.; Ogura, H.; Ishii, Y.; Koisumi, T. J. Chem. Soc. Perkin Trans. I 1989, 1721.
27. (c) Barelle M.; Hamman, S. J. Chem. Res. (M) 1990, 701.
28. Aldrich, 2.5M in hexanes.
29. 11 (2 mmol) was added onto the chiral 3-aminopyrrolidine 3 (0.75 mmol) in THF (17 mL) at -20°C; after 30 min at this temperature, the mixture was cooled down to -78°C and the THF solution of the aldehyde (0.5 mmol in 1 mL of THF) injected slowly. The medium was quenched (3 mL of 3N HCl) after 3h.
30. Colon, D. F.; Pickard, S. T.; Smith, H. E. J. Org. Chem. 1991, 56, 2322.
31. Weber, B.; Seebach, D. Tetrahedron 1994, 50, 7473. These authors obtain the best selectivities in the following order: benzaldehyde 〉 o-tolualdehyde 〉 o-methoxybenzaldehyde.
32. (a) Seebach, D.; Weber, T. Tetrahedron Lett. 1983, 24, 3315.
33. (b) Comins, D. L.; Brown, J. D. Tetrahedron Lett. 1981, 22, 4213.
34. (c) Comins, D. L.; Brown, J. D.; Mantlo, N. B. Tetrahedron Lett. 1982, 23, 3979.
35. (d) Comins, D. L. Synlett 1992, 615.
36. Fraenkel, G.; Henrichs, M.; Hewitt, J. M.; Su, B. M.; Geckle, M. J. J. Am. Chem. Soc. 1980, 102, 3345.
37. 3OD at 25°C.
38. Henderson, K. W.; Walther, D. S.; Williard, P. G. J. Am. Chem. Soc. 1995, 117, 8680.