Addition of allylmetal reagents to the imine derived from 2-pyridine carboxaldehyde and methyl (S)-valinate. Synthesis of (S)- and (R)-1-(2-pyridyl)-3-butenamine

Tetrahedron Asymmetry

Volumn 7, Issue 7, 1996, Pages 2083-2092

  Alvaro, Giuseppe ^a   Savoia, Diego ^a  

^a UNIVERSITY OF BOLOGNA   (Italy)

Author keywords

[No Author keywords available]

Indexed keywords

PYRIDINE DERIVATIVE;

ARTICLE; DRUG PURITY; DRUG SYNTHESIS; ENANTIOMER; INFRARED SPECTROPHOTOMETRY; NUCLEAR MAGNETIC RESONANCE; PRIORITY JOURNAL; REACTION ANALYSIS;

EID: 0030200995     PISSN: 09574166     EISSN: None     Source Type: Journal    
DOI: 10.1016/0957-4166(96)00251-0     Document Type: Article

References (43)

1. 1. (a)Volkmann, R. A. in Comprehensive Organic Synthesis, B. M. Trost, Ed.; Pergamon Press: Oxford and New York, 1991; Vol. 1, Ch. 1.12, p. 356-396.
2. (b) Roush, W. R. in Comprehensive Organic Synthesis, B. M. Trost, Ed.; Pergamon Press: Oxford and New York, 1991; Vol.2, Ch. 1.1, p. 1-49.
3. (c) Kleinmann, E. F.; Volkmann, R. A. in Comprehensive Organic Synthesis, B. M. Trost, Ed.; Pergamon Press: Oxford and New York; 1991, Vol. 2, Ch. 4.3, p. 975-1006.
4. (d) Yamamoto, Y.; Asao, N. Chem. Rev. 1993, 93, 2207.
5. 2. Basile, T.; Bocoum, A.; Savoia, D.; Umani-Ronchi, A. J. Org. Chem. 1994, 59, 7766.
6. 3. Yamamoto, Y.; Komatsu, T.; Maruyama, K. J. Am. Chem. Soc. 1986, 108, 7778.
7. 4. Hallet, D. J.; Thomas, E. J. J. Chem. Soc., Chem. Commun. 1995, 657.
8. 5. Alvaro, G.; Boga, C.; Savoia, D.; Umani-Ronchi, A. J. Chem. Soc., Perkin Trans. 1 1996. 0000.
9. 2 to (S)-3 (THF, -78 °C) gave the (R, S)-homoallylic amine with 70% de; the same reagent did not add the analogous corresponding imines derived from 3-and 4-pyridine carboxaldehyde.
10. 7. (a) Brunner, H.; Reiter, B.; Riepl, G. Chem. Ber. 1984, 117, 1330.
11. (b) Eleveld, M. B.; Hogeven, H.; Tetrahedron Lett. 1984, 25, 5187.
12. (c) Brunner, H.; Fisch, H. J. Organomet. Chem. 1987, 335, 1.
13. (d) Brunner, H.; Fisch, H. J. Organomet. Chem. 1987, 335, 15.
14. (e) Brunner, H.; Fisch, H. Monatsh. Chem. 1988, 119, 525.
15. (f) Chelucci, G.; Conti, S.; Falorni, M.; Giacomelli, G. Tetrahedron 1991, 47, 8251.
16. (g) Chelucci, G. Gazz. Chim. Ital. 1992, 112, 89.
17. (h) Falorni, M.; Giacomelli, G. ibid. 1992, 122, 339.
18. (i) Conti, S.; Falorni, M.; Giacomelli, G.; Soccolini, F. Tetrahedron 1992, 48, 8993.
19. (j) Bernauer, K.; Chuard, T.; Stoeckli-Evans, H. Helv. Chim. Acta 1993, 76, 2263;
20. (k) Cabras, M. A.; Chelucci, G.; Giacomelli, G.; Soccolini, F. Gazz. Chim. Ital. 1994, 124, 23.
21. 8. Mi, A.; Xiao, X.; Wu, L.; Jiang, Y. Synth. Commun 1992, 21, 2207.
22. 9. Chang, Z.-Y; Coates, R. M. J. Org. Chem. 1990, 55, 3475.
23. 3 and THF.
24. 11. Lambert, F.; Kirschleger, B.; Villiéras, J. J. Organometal. Chem. 1991, 405, 273.
25. 2 frees previously coordinated carbonyl group to produce the N,N-chelation complex: Maughan, D.; Wardell, J. L. J. Organometal. Chem. 1981, 212, 59.
26. 13. (a) Tsapkov, V. I.; Popov, M. S.; Fung, F. N.; Samus, N. M. Russ. J. Gen. Chem. 1994, 64, 578;
27. (b) Tsapkov, V. I.; Samus, N. M. Russ. J. Gen. Chem. 1994, 64, 721;
28. (c) Samus, N. M.; D'erd', P.; Tsapkov, V. I. Russ. J. Gen. Chem. 1994, 64, 721.
29. (c) Hsu, C. C.; Geanangel, R. A. Inorg. Chem. 1980, 19, 110.
30. (d) Matsubayashi, G.-E.; Hiroshima, M.; Tanaka, T. J. Inorg. Nucl. Chem. 1971, 33, 3787; 12.
31. 14. Fouquet, E.; Gabriel, A.; Maillard, B.; Pereyre, M. Bull. Soc. Chim. Fr. 1995, 132, 590.
32. 15. Neumann, W.; Rogic, M. M.; Dunn, T. J. Tetrahedron Lett. 1991, 32, 5865.
33. 16. van Maanen, H. L.; Kleijn, H.; Jastrzebski, J. T. B. H.; Lakin, M. T.; Spek, A. L.; van Koten, G. J. Org. Chem. 1994, 59, 7839.
34. 17. (a) Reinhold, J.; Benedix, R.; Birner, P.; Henning, H. Inorg. Chim. Acta 1979, 33, 209.
35. (b) van Koten, G.; Vrieze, K. Adv. Organomet. Chem. 1982, 21, 151.
36. (c) Kaim, W. Acc. Chem. Res. 1985, 18, 160.
37. 18. (a) Giezynski, R.; Pasynkiewicz, S.; Serwatowska, A. J. Organomet. Chem. 1974, 69, 345.
38. (b) Klerks, J. M.; Stufkens, D. J.; van Koten, G.; Vrieze, K. J. Organomet. Chem. 1979, 181, 271.
39. (c) Klerks, J. M.; Jastrzebski, J. T. B. H.; van Koten, G.; Vreeze, K. J. Organomet. Chem. 1982, 224, 107.
40. (d) van Koten, G.; Jastrzebski, J. T. B. H.; Vrieze, K. J. Organomet. Chem. 1983, 250, 49.
41. (e) Stamp, L.; tom Dieck, H. J. Organomet. Chem. 1984, 277, 297.
42. (f) Wissing, E.; Kleijn, H.; Boersma, J.; van Koten, G. Recl. Trav. Chim. Pays-Bas 1993, 112, 618.
43. (g) Wissing, E.; Kaupp, M.; Boersma, J.; Spek, A. L.; van Koten, G. Organometallics 1994, 13, 2349.