Conformational analysis of MNCB (MBNC) esters and amides: Promising chiral reagents for stereoselective applications

Tetrahedron

Volumn 55, Issue 23, 1999, Pages 7305-7318

  Latypov, Shamil K ^a   Aganov, Albert V ^b   Tahara, Satoshi ^c   Fukushi, Yukiharu ^c  

^a A E ARBUZOV INSTITUTE OF ORGANIC AND PHYSICAL CHEMISTRY   (Russian Federation)

^b KAZAN FEDERAL UNIVERSITY   (Russian Federation)

^c HOKKAIDO UNIVERSITY   (Japan)

Author keywords

[No Author keywords available]

Indexed keywords

AMIDE; BENZOIC ACID DERIVATIVE; ESTER DERIVATIVE;

ANISOTROPY; ARTICLE; CHEMICAL BOND; CHEMICAL STRUCTURE; CONFORMATION; CONFORMATIONAL TRANSITION; DIASTEREOISOMER; PRIORITY JOURNAL; PROTON NUCLEAR MAGNETIC RESONANCE; STEREOCHEMISTRY; TEMPERATURE DEPENDENCE;

EID: 0033522862     PISSN: 00404020     EISSN: None     Source Type: Journal    
DOI: 10.1016/S0040-4020(99)00356-7     Document Type: Article

References (58)

1. a) G. Uray in Houben-Weyl Methods in Organic Chemistry, Vol. 1 (G.Helchen, R.W.Hoffmann, J.Mulzer, E.Schaumann, Ed), Thieme, Stuttgart - N.York, 1996.
2. b) Eliel, E.L.; Wilen, S.H.; Mander, L.N. Stereochemistry of Organic Compounds, Wiley-Interscience, 1994.
3. a) Raban, M.; Mislow, K. Tetrahedron Letters. 1965, 48, 4249.
4. b) Raban, M.; Mislow, K. Top. Stereochemistry. 1967, 2, 199.
5. c) Dale, J.A.; Mosher, H.S. J. Am. Chem. Soc. 1968, 90, 3732.
6. d) Dale, J.A.; Mosher, H.S. J. Am. Chem. Soc. 1973, 95, 512.
7. e) Dale, J.A.; Dull, D.L.; Mosher, H.S. J. Org. Chem. 1969, 34, 2543.
8. f) Sullivan, G.R.; Dale, J.A.; Mosher, H.S. J. Org. Chem. 1973, 38, 2143.
9. a) Trost, B. M.; Belletire, J. L.; Godleski, S.; McDougal, P. G.; Balkovec, J. M. J. Org. Chem. 1986, 51, 2370.
10. b) Trujillo, M.; Morales, E.Q.; Vazquez, J.T. J. Org. Chem. 1994, 59, 6637.
11. c) Oshikawa, T.; Yamashita, M.; Kumagai, S.; Seo, K.; Kabayashi, J. J. Chem. Soc. Commun. B 1995, 435.
12. d) Latypov, Sh. K.; Riguera, R.; Smith, M.B.; Polivkova. J. J. Org. Chem, In Press.
13. e) Alexakis, A.; Frutos, J. C.; Mutti, S.; Mangeney, P. J. Org. Chem., 1994, 59, 3326.
14. f) Heumann, A.; Faure, R. J. Org. Chem., 1993, 58, 1276.
15. g) Doolittle, R. E.; Heath, R. R. J. Org. Chem., 1984, 49, 5041.
16. a) Waugh, J.S.; Fessenden, R.W. J. Am. Chem. Soc. 1957, 79, 846.
17. b) Johnson. C.E.; Bovey, F.A. J. Chem. Phys. 1958, 29, 1012.
18. c) Jonathan, N.; Gordon, S.; Dailey, B.P. J. Chem. Phys. 1962, 36, 2443;
19. d) Dailey, B. P. J. Chem. Phys., 1964, 41, 2304;
20. e) Musher, J. I. J. Chem. Phys., 1965, 42, 4081;
21. f) Haigh, C.W.; Mallion, R.B. "Ring Cuarrent Theories in NMR" Progress in NMR Spectroscopy, (Pergamon Press Ltd.), 1980,13, 303.
22. a) Trost, B. M.; Bunt, R. C.; Pulley, Sh. R. J. Org. Chem., 1994, 59, 4202.
23. b) Latypov, Sh. K., Seco, J.M., Quinoa, E., Riguera. R. J. Org. Chem. 1995, 60, 1538.
24. c) Ferreiro, M. J., Latypov, Sh. K., Quinoa, E., Riguera. R. J. Tetrahedron Asym., 1996, 7(8), 2195.
25. d) Latypov, Sh. K., Ferreiro, M. J., Quinoa, E., Riguera. R. J. Am. Chem. Soc., Submitted for publication.
26. e) Ferreiro, M. J., Latypov, Sh. K., Quinoa, E., Riguera. R. J. Tetrahedron Asym., 1997, 8(7), 1015.
27. a) Latypov, Sh. K., Seco, J.M., Quinoa, E., Riguera. R. J. Org. Chem. 1995, 60, 504.
28. b) Seco, J.M.; Latypov, Sh.K.; Quinoa, E.; Riguera, R. Tetrahedron Letters., 1994, 35 (18), 2921.
29. c) Seco, J. M.; Latypov, Sh. K.; Quinoa, E.; Riguera, R. Tetrahedron Asym. 1995, 6, 107.
30. d) Kusumi, T.; Takahashi, H.; Xu, P.; Fukushima, T.; Asakawa, Y.; Hashimoto, T.; Kau, Y.; Inonyc, Y. Tetrahedron Lett., 1994, 35, 4397.
31. e) Kuroda, K.; Kusumi, T.; Ping, X.; Kan, Y.; Hashimoto, T.; Asakawa, Y. Tetrahedron Lett., 1996, 37, 4541.
32. f) Seco, J.M., Latypov, Sh. K., Quinoa, E., Riguera. R. Tetrahedron, 1997, 53, 8541.
33. a) Miyano, S., Okada, Sh., Hotta, H., Takeda, M., Suzuki, T., Kabuto, Ch., Yasuharu, F. Bull. Chem. Soc. Jpn., 1989, 62, 3886.
34. b) Fukushi, Yu.; Yajima, Ch.; Mizutani, Ju. Tetrahedron Letters., 1994, 35 (4), 599.
35. c) Fukushi, Y.; Yajima, C.; Mizutani, J. Tetrahedron Lett., 1994, 35, 9417.
36. d) Fukushi, Y.; Shigematsu, K.; Mizutani, J.; Tahara, S. Tetrahedron Lett., 1996, 37, 4737.
37. ;RS = δ(R) -δ(S)].
38. a) Farnell, L.; Pople, J.A.; Radom, L. J. Phys. Chem. 1983, 87, 79.
39. b) Pople, J.A. Ber. Bunsenges. Phys. Chem. 1982, 86, 806.
40. c) De Frees, D.J.; Raghavachari, K.; Pople, J.A. J. Am. Chem. Soc, 1982, 104, 5576
41. a) Blanchard-Desce, M.; Alain, V.; Bedworth, P.V.; Marder, S.R.; Fort, A.; Runser, C.; Barzoulas, M.; Lebus, S.; Worthmann, R. Chem. Evr. J. 1997, 3, 1091.
42. b) Albert, I.D.L.; Marks, T.J.; Ratner, M.A. J. Phys. Chem. 1996, 100, 9714.
43. c) Di Bella, S.; Marks, T.J.; Ratner, M.A. J. Am. Chem. Soc, 1994, 116, 4440.
44. d) Dehu, Ch.; Geskin, V.; Persons, A.; Bredas, J.-L. Eur. J. Org. Chem. 1998, 1267
45. a) Latypov, Sh. K., Seco, J.M., Quinoa, E., Riguera. R. J. Org. Chem. 1996, 61, 8569.
46. b) Seco, J.M., Latypov, Sh. K., Quinoa, E., Riguera. R. J. Org. Chem., 1997, 62, 7569
47. This work under process and complete results will be published elsewhere.
48. a) Drakenberg, T., Jost, R., Sommer, J. M. J. Chem. Soc. Perkin II, 1975, 1682.
49. b) Lunazzi, L., Ticca, A., Macciantelli, D., Spunta, G. J. Chem. Soc. Perkin II, 1976, 1121.
50. c) Benassi, R., Iarossi, D., Folii, U., Schenetti, L., Taddei, F. J. Chem. Soc. Perkin II, 1981, 228.
51. Maple, J.R.; Dinur, U.; Hagler, A.T. Proc. Natl. Acad. Sci. U.S.A., 1988, 85(15), 5350;
52. Cioslowski, J.; Kertesz, M. QCPE Bull. 1987, 7, 159
53. a) Dewar, M.J.S.; Zoebisch, E.G.; Healy, E.F.; Stewart, J.J.P. J. Am. Chem. Soc. 1985, 107, 3902;
54. b) Havel, T.F. Prog. Biophys. Mol. Biol. 1991, 56, 43;
55. c) Stewart, J.J.P. J. Computational. Chem. 1989, 10, 209;
56. d) Komorinski, A.; McIver, Jr.W. Jr. J. Am. Chem. Soc. 1973, 95, 4512.
57. GAUSSIAN 92, Revision D.1, M.J. Frisch, G.W.trucks, M. Head-Gordon, P.M.W. Gill, M.W. Wrong, J.B. Foresman, B.G. Johnson, H.B. Shlegel, M.A. Robb, E.S. Replogle, R. Gomperts, J.L. Andres, K. Raghavachari, J.S. Binkley, C. Gonzalez, R.L. Martin, D.J. Fox, D.J. Defrees, J. Baker, J.J.P. Stewart, and J.A. Pople, Gaussian, Inc., Pittsburgh PA, 1992.
58. Hassner, A.; Alexanian, V. Tetrahedron Lett., 1978, 4475.