A novel mixed dimer of a norephedrine-derived chiral lithium amide and 2-lithium-1-methylimidazole, and catalytic enantioselective deprotonation of cyclohexene oxide

Chemistry - A European Journal

Volumn 7, Issue 20, 2001, Pages 4368-4377

  Amedjkouh, Mohamed ^a   Pettersen, Daniel ^a   Nilsson Lill, Sten O ^a   Davidsson, Öjvind ^a   Ahlberg, Per ^a  

^a UNIVERSITY OF GOTHENBURG   (Sweden)

Author keywords

Asymmetric catalysis; Chiral lithium amide; Heterodimer; Multinuclear (1H, 6Li, 13C) NMR; Semiempirical calculations

Indexed keywords

CATALYSIS; MOLECULAR STRUCTURE; NUCLEAR MAGNETIC RESONANCE;

DEPROTONATION;

DIMERS;

1 METHYLIMIDAZOLE; 1-METHYLIMIDAZOLE; 2 CYCLOHEXENONE; 2 LITHIUM 1 METHYLIMIDAZOLE; ADRENERGIC ALPHA AGONISTS; ALPHA ADRENERGIC RECEPTOR STIMULATING AGENT; AMIDE; CARBENOID; CYCLOHEXANE DERIVATIVE; CYCLOHEXANE OXIDE; DIMER; IMIDAZOLE DERIVATIVE; LITHIUM; LITHIUM DERIVATIVE; NITROGEN; NOREPHEDRINE; ORGANOMETALLIC COMPOUND; PHENYLPROPANOLAMINE; UNCLASSIFIED DRUG;

ARTICLE; CARBON NUCLEAR MAGNETIC RESONANCE; CATALYSIS; CHEMICAL STRUCTURE; CHEMISTRY; CHIRALITY; DIMERIZATION; ENANTIOMER; PROTON NUCLEAR MAGNETIC RESONANCE; SOLVATION; STEREOCHEMISTRY; STEREOISOMERISM; SYNTHESIS;

ADRENERGIC ALPHA-AGONISTS; CATALYSIS; CYCLOHEXANES; CYCLOHEXENES; DIMERIZATION; IMIDAZOLES; LITHIUM; MODELS, MOLECULAR; ORGANOMETALLIC COMPOUNDS; PHENYLPROPANOLAMINE; STEREOISOMERISM;

EID: 0035886822     PISSN: 09476539     EISSN: None     Source Type: Journal    
DOI: 10.1002/1521-3765(20011015)7:20<4368::AID-CHEM4368>3.0.CO;2-K     Document Type: Article

References (41)

1. N. S. Simpkins, Pure Appl. Chem. 1996, 68, 691.
2. D. M. Hodgson, A. R. Gibbs, G. P. Lee, Tetrahedron 1996, 52, 14 361.
3. P. O'Brien, J. Chem. Soc. Perkin Trans. 1 1998, 1439.
4. T. Kasai, H. Watanabe, K. Mori, Bioorg. Med. Chem. 1993, 1, 67.
5. M. Asami, S. Inoue, Tetrahedron 1995, 51, 11 725.
6. D. M. Hodgson, A. R. Gibbs, Synlett 1997, 657.
7. D. M. Hodgson, J. Witherington, B. A. Moloney, J. Chem. Soc. Perkin Trans. 1 1994, 3373.
8. M. Asami, J. Takahashi, S. Inoue, Tetrahedron: Asymmetry 1994, 5, 1649.
9. D. Bhuniya, A. DattaGupta, V. K. Singh, J. Org. Chem. 1996, 61, 6108.
10. G. Hilmersson, P. I. Arvidsson, Ö. Davidsson, M. Håkansson, Organometallics 1997, 16, 3352.
11. G. Hilmersson, P. I. Arvidsson, Ö. Davidsson, M. Håkansson, J. Am. Chem. Soc. 1998, 120, 8143.
12. P. I. Arvidsson, G. Hilmersson, P. Ahlberg, J. Am. Chem. Soc. 1999, 121, 1883.
13. D. Sato, H. Kawasaki, I. Shimada, Y. Arata, K. Okamura, T. Date, K. Koga, Tetrahedron 1997, 53, 7191.
14. G. Hilmersson, Ö. Davidsson, J. Org. Chem. 1995, 60, 7660.
15. J. P. Tierney, A. Alexakis, P. Mangeney, Tetrahedron: Asymmetry 1997, 8, 1019.
16. M. Amadji, J. Vadecard, J.-C. Plaquevent, L. Duhamel, P. Duhamel, J. Am. Chem. Soc. 1996, 118, 12 483.
17. T. Yamashita, D. Sato, T. Kiyoto, A. Kumar, K. Koga, Tetrahedron 1997, 53, 16 987.
18. M. Asami, T. Ishizaki, S. Inoue, Tetrahedron: Asymmetry 1994, 5, 793.
19. M. Asami, T. Suga, K. Honda, S. Inoue, Tetrahedron Lett. 1997, 38, 6425.
20. M. J. Södergren, P. G. Andersson, J. Am. Chem. Soc. 1998, 120, 10 760.
21. M. J. Södergren, S. K. Bertilsson, P. G. Andersson, J. Am. Chem. Soc. 2000, 122, 6610.
22. C. Hilf, F. Bosold, K. Harms, J. C. W. Lohrenz, M. Marsch, M. Schimeczek, G. Boche, Chem. Ber. 1997, 130, 1201.
23. C. Hilf, F. Bosold, K. Harms, M. Marsch, G. Boche, Chem. Ber. 1997, 130, 1213.
24. D. Pettersen, M. Amedjkouh, S. O. Nilsson Lill, K. Dahlén, P. Ahlberg, J. Chem. Soc. Perkin Trans. 2 2001, Published on the Web 27th of April.
25. S. E. De Sousa, P. O'Brien, H. C. Steffens, Tetrahedron Lett. 1999, 40, 8423.
26. S. O. Nilsson Lill, P. I. Arvidsson, P. Ahlberg, Tetrahedron: Asymmetry 1999, 10, 265.
27. A. Abbotto, A. Streitwieser, P. v. R. Schleyer, J. Am. Chem. Soc. 1997, 119, 11 255.
28. E. Kaufmann, J. Gose, P. v. R. Schleyer, Organometallics 1989, 8, 2577.
29. G. Hilmersson, Ö. Davidsson, Organometallics 1995, 14, 912.
30. D. Zhao, C.-y. Chen, F. Xu, L. Tan, R. Tillyer, M. E. Pierce, J. R. Moore, Org. Synth. 2000, 77, 12.
31. E. Anders, R. Koch, P. Freunscht, J. Comput. Chem. 1993, 14, 1301.
32. J. J. P. Stewart, J. Comput. Chem. 1989, 10, 209.
33. W. J. Hehre, B. J. Deppmeier, A. J. Driessen, J. A. Johnson, P. E. Klunzinger, L. Lou, J. Yu, J. Baker, J. E. Carpenter, R. W. Dixon, S. S. Fielder, H. C. Johnson, S. D. Kahn, J. M. Leonard, W. J. Pietro, Spartan v. 5.0.1, Wavefunction Inc., Irvine, CA, 1997.
34. W. Huang, personal communication, 13. 5. 1998.
35. G. I. Csonka, J. Comput. Chem. 1993, 14, 895.
36. G. I. Csonka, J. G. Angyan, THEOCHEM 1997, 393, 31.
37. A. D. Becke, J. Chem. Phys. 1993, 98, 5648.
38. C. Lee, W. Yang, R. G. Parr, Phys. Rev. B: Condens. Matter 1988, 37, 785.
39. R. Krishnan, J. S. Binkley, R. Seeger, J. A. Pople, J. Chem. Phys. 1980, 72, 650.
40. M. J. Frisch, J. A. Pople, J. S. Binkley, J. Chem. Phys. 1984, 80, 3265.
41. Gaussian 98 (Revision A.7), M. J. Frisch, G. W. Trucks, H. B. Schlegel, G. E. Scuseria, M. A. Robb, J. R. Cheeseman, V. G. Zakrzewski, J. A. Montgomery, R. E. Stratmann, J. C. Burant, S. Dapprich, J. M. Millam, A. D. Daniels, K. N. Kudin, M. C. Strain, O. Farkas, J. Tomasi, V. Barone, M. Cossi, R. Cammi, B. Mennucci, C. Pomelli, C. Adamo, S. Clifford, J. Ochterski, G. A. Petersson, P. Y. Ayala, Q. Cui, K. Morokuma, D. K. Malick, A. D. Rabuck, K. Raghavachari, J. B. Foresman, J. Cioslowski, J. V. Ortiz, B. B. Stefanov, G. Liu, A. Liashenko, P. Piskorz, I. Komaromi, R. Gomperts, R. L. Martin, D. J. Fox, T. Keith, M. A. Al-Laham, C. Y. Peng, A. Nanayakkara, C. Gonzalez, M. Challacombe, P. M. W. Gill, B. G. Johnson, W. Chen, M. W. Wong, J. L. Andres, M. Head-Gordon, E. S. Replogle, J. A. Pople, Gaussian, Inc., Pittsburgh PA, 1998.