Mixed complexes formed by lithioacetonitrile and chiral lithium amides: Observation of 6Li,15N and 6Li,13C couplings due to both C-Li and N-Li contacts

Journal of the American Chemical Society

Volumn 126, Issue 21, 2004, Pages 6798-6805

  Sott, Richard ^a   Granander, Johan ^a   Hilmersson, Göran ^a  

^a UNIVERSITY OF GOTHENBURG   (Sweden)

Author keywords

[No Author keywords available]

Indexed keywords

COMPLEXATION; DIMERS; NEGATIVE IONS; NUCLEAR MAGNETIC RESONANCE SPECTROSCOPY; SOLVENTS;

LITHIUM SALTS; TRIMERS;

LITHIUM COMPOUNDS;

ACETONITRILE; AMIDE; CARBON; ETHER; KETENE DERIVATIVE; LITHIOACETONITRILE; LITHIUM; LITHIUM N (2 METHOXYBENZYL) 1 AMINO 1 PHENYL 2 ETHOXYETHANE; LITHIUM N ISOPROPYL 2 AMINO 1 PHENYL 3 METHOXYPROPANE; NITROGEN; TETRAHYDROFURAN; UNCLASSIFIED DRUG;

ARTICLE; CARBON NUCLEAR MAGNETIC RESONANCE; CHIRALITY; COMPLEX FORMATION; DIMERIZATION; ISOTOPE LABELING; NUCLEAR MAGNETIC RESONANCE SPECTROSCOPY;

EID: 2542514849     PISSN: 00027863     EISSN: None     Source Type: Journal    
DOI: 10.1021/ja0388461     Document Type: Article

References (60)

1. (a) Noyori, R. Asymmetric Catalysis in Organic Synthesis; John Wiley & Sons: New York, 1994.
2. (b) Comprehensive Asymmetric Catalysis; Jacobsen, E. N., Pfaltz, A., Yamamoto, H., Eds.; H. Springer: Berlin, 1999.
3. (a) Kozaki, H.; Aratani, T.; Toraya, T. Tetrahedron Lett. 1968, 9, 4097.
4. (b) Mukaiyama, T.; Soai, K.; Sato, T.; Shimizu, H.; Suzuki, K. J. Am. Chem. Soc. 1979, 101, 1455.
5. (c) Mazaleyrat, J.-P.; Cram, D. J. J. Am. Chem. Soc. 1981, 103, 4585.
6. (d) Corruble, A.; Valnot, J.-Y.; Maddaluno, J.; Duhamel, P. J. Org. Chem. 1997, 63, 88266.
7. (e) Corruble, A.; Valnot, J.-Y.; Maddaluno, J.; Prigent, Y.; Davoust, D. ; Duhamel, P. J. Am. Chem. Soc. 1997, 119, 10042.
8. (f) Arvidsson, P. I.; Davidsson, Ö.; Hilmersson, G. Tetrahedron: Asymmetry 1999, 10, 527.
9. (g) Arvidsson, P. I.; Hilmersson, G.; Davidsson, Ö. Chem. Eur. J. 1999, 5, 2348.
10. (h) Granander, J.; Sott, R.; Hilmersson, G. Tetrahedron: Asymmetry 2003, 14, 439.
11. Eleveld, M. B.; Hogeveen, H. Tetrahedron Lett. 1984, 25, 5187.
12. (a) Hilmersson, G.; Davidsson, Ö. Organometallics 1995, 14, 912.
13. (b) Hilmersson, G.; Davidsson, Ö. J. Organomet. Chem. 1995, 489, 175.
14. (c) Hoffman, D.; Collum, D. B. J. Am. Chem. Soc. 1998, 120, 5810.
15. (d) Hilmersson, G.; Malmros, B. Chem. Eur. J. 2001, 7, 337.
16. (e) Lucht, B. L.; Bernstein, M. P.; Remenar, J. F.; Collum, D. B. J. Am. Chem. Soc. 1996, 118, 10707.
17. (f) Corruble, A.; Davoust, D.; Desjardins, S.; Fressigné, C.; Giessner-Prettre, C.; Harrison-Marchand, A.; Houte, H.; Lasne, M.-C.; Maddaluno, J.; Oulyadi, H.; Valnot, J.-Y. J. Am. Chem. Soc. 2002, 124, 15267.
18. (a) Hilmersson, G.; Arvidsson, P. I.; Davidsson, O.; Håkansson, M. J. Am. Chem. Soc. 1998, 120, 8143.
19. (b) Hilmersson, G.; Arvidsson, P. I.; Davidsson, Ö.; Håkansson, M. Organometallics 1997, 16, 3352.
20. (a) Hilmersson, G.; Davidsson, Ö. J. Am. Chem. Soc. 1995, 60, 7660.
21. (b) Hilmersson, G. Chem. Eur. J. 2000, 6, 3069.
22. (a) Bauer, W.; Seebach, D. Helv. Chim. Acta 1984, 67, 1972.
23. (b) Boche, G. Angew. Chem., Int. Ed. 1989, 28, 277.
24. (c) Das, R.; Wilkie, C. J. Am. Chem. Soc. 1972, 94, 4555.
25. (d) Boche, G.; Marsch, M.; Harms, K. Angew. Chem., Int. Ed. 1986, 4, 373-374.
26. (e) Crowley, P. J.; Leach, M. R.; Meth-Cohn, O.; Wakefield, B. J. Tetrahedron Lett. 1986, 27, 2909.
27. (f) Kaneti, J.; Schleyer, P. v. R.; Clark, T.; Kos, A. J.; Spitznagel, G. W.; Andrade, J. G.; Moffat, J. B. J. Am. Chem. Soc. 1986, 108, 1481.
28. (g) Carlier, P. R.; Madura, J. D. J. Org. Chem. 2002, 67, 3832.
29. (h) Boche, G.; Langlotz, I.; Marsch, M.; Harms, K.; Frenkling, G. Angew. Chem., Int. Ed. 1993, 32, 1171.
30. (i) Lambert, C.; Schleyer, P. v. R.; Pieper, U.; Stalke, D. Angew. Chem., Int. Ed. 1992, 31, 77.
31. (j) Koch, R.; Wiedel, B.; Anders, E. J. Org. Chem. 1996, 61, 2523.
32. (k) Carlier, P. R.; Lucht, B. L.; Collum, D. B. J. Am. Chem. Soc. 1994, 116, 116023.
33. (l) Enders, D.; Kirchhoff, J.; Gerdes, P.; Mannes, D.; Raabe, G.; Runsink, J.; Boche, G.; Marsch, M.; Ahlbrecht, H.; Sommer, H. Eur. J. Org. Chem. 1998, 1, 63.
34. (m) Carlier, P. R.; Lo, C. W.-S. J. Org. Chem. 2000, 67, 3832.
35. Boche, G.; Harms, K.; Marsch, M. J. Am. Chem. Soc. 1988, 110, 6925.
36. Sott, R.; Granander, J.; Hilmersson, G. Chem. Eur. J. 2002, 8, 2081.
37. (a) Kallman, N.; Collum, D. B. J. Am. Chem. Soc. 1987, 109, 7466.
38. (b) Jackman, L. M.; Scarmoutzos, L. M.; Porter, W. J. Am. Chem. Soc. 1987, 109, 6772.
39. (c) Galiano-Roth, A. S.; Michaelides, E. M.; Collum, D. B. J. Am. Chem. Soc. 1989,111, 6772.
40. (d) Sato, D.; Kawasaki, H.; Shimada, I.; Arata, Y.; Okamura, K.; Date, T.; Koga, K. J. Am. Chem. Soc. 1992, 114, 761.
41. (e) Lucht, B. L.; Collum, D. B. Acc. Chem. Res. 1999, 32, 1035.
42. (f) Arvidsson, P. I.; Davidsson, Ö. Angew. Chem., Int. Ed. 2000, 39, 1467.
43. (a) Bauer, W.; Schleyer, P. v. R. Magn. Reson. Chem. 1988, 26, 827.
44. (b) Bauer, W.; Müller, G.; Pi, R.; Schleyer, P. v. R. Angew. Chem., Int. Ed. Engl. 1986, 25, 1103.
45. (c) Bauer, W.; Winchester, W. R.; Schleyer, P. v. R. Organometallics 1987, 6, 2371.
46. (a) Jeener, J.; Meier, B. H.; Bachmann, P.; Ernst, R. R. J. Chem. Phys. 1979, 71, 4546.
47. (b) Meier, B. H.; Ernst, R. R. J. Am. Chem. Soc. 1979, 101, 6441.
48. (c) Abel, E. W.; Coston, T. P. J.; Orrel, K. G.; Sik, V.; Stephenson, D. J. Magn. Reson. 1986, 70, 34.
49. (a) Ahlberg, P.; Karlsson, A.; Davidsson, Ö.; Hilmersson, G.; Löwendahl, J.-M. J. Am. Chem. Soc. 1997, 119, 1751.
50. (b) Rumpel, H.; Limbach, H.-H. J. Am. Chem. Soc. 1989, 111, 5429.
51. (c) Reich, H. J.; Goldenberg, W. S.; Sanders, A. W.; Jantzi, K. L.; Tzschucke, C. C., J. Am. Chem. Soc. 2003, 125, 3509.
52. (a) Fraenkel, G.; Henrichs, M.; Hewitt, J. M.; Su, B. M.; Geckle, M. J. J. Am. Chem. Soc. 1980, 102, 3345.
53. (b) Fraenkel, G.; Henrichs, M.; Hewitt, J. M.; Su, B. M. J. Am. Chem. Soc. 1984, 106, 255.
54. (c) Thomas, R. D.; Clarke, M. T.; Jensen, R. M.; Young, C. Organometallics 1986, 5, 1851.
55. (d) Bauer, W.; Griesinger, C. J. Am. Chem. Soc. 1993, 115, 10871.
56. (a) Davidsson, Ö.; Löwendahl, J.-M.; Ahlberg, P. J. Chem. Soc., Chem. Commun. 1992, 1004.
57. (b) Fraenkel, G.; Martin, K.; J. Am. Chem. Soc. 1995, 117, 10336.
58. (c) Fraenkel, G.; Duncan, J. H.; Martin, K.; Wang, J. J. Am. Chem. Soc. 1999, 121, 10538.
59. Granander, J.; Sott, R.; Hilmersson, G. Tetrahedron 2002, 58, 4717.
60. Engdahl, C.; Ahlberg, P. J. Am. Chem. Soc. 1979, 101, 3940