Rotational features of carbon-nitrogen bonds in axially chiral o-tert- butyl anilides and related molecules. Potential substrates for the 'prochiral auxiliary' approach to asymmetric synthesis

Tetrahedron Asymmetry

Volumn 8, Issue 23, 1997, Pages 3955-3975

  Curran, Dennis P ^a   Hale, Gregory R ^a   Geib, Steven J ^a   Balog, Aaron ^a   Cass, Quezia B ^b   Degani, Ana Luiza G ^b   Hernandes, Marcelo Z ^b   Freitas, Luiz Carlos G ^b  

^a UNIVERSITY OF PITTSBURGH   (United States)

^b FEDERAL UNIVERSITY OF SÃO CARLOS   (Brazil)

Author keywords

[No Author keywords available]

Indexed keywords

ANILIDE;

ARTICLE; CHIRAL CHROMATOGRAPHY; CHIRALITY; PRIORITY JOURNAL; PROTON NUCLEAR MAGNETIC RESONANCE; ROTATION; SYNTHESIS;

EID: 0031438042     PISSN: 09574166     EISSN: None     Source Type: Journal    
DOI: 10.1016/S0957-4166(97)00599-5     Document Type: Article

References (46)

1. (a) Seyden-Penne, J. Chiral Auxiliaries and Ligands in Asymmetric Synthesis; Wiley: NY, 1995.
2. (b) Nógrády, M. Stereoselective Synthesis; VCH: WeinHeim, 1995.
3. (c) Procter, G. Asymmetric Synthesis; Oxford University Press: Oxford, 1996.
4. Rosini, C.; Franzini, L.; Raffaelli, A.; Salvadori, P. Synthesis 1992, 503.
5. Ito, Y. N.; Ariza, X.; Beck, A. K.; Bohac, A.; Ganter, C.; Gawley, R. E.; Kühnle, F. N. M.; Tuleja, J.; Wang, Y. M.; Seebach, D. Helv. Chim. Acta 1994, 77, 2071.
6. Seebach, D.; Sting, A. R.; Hoffmann, M. Angew. Chem. Int. Ed. Eng. 1997, 35, 2708.
7. Reviews: (a) Noyori, R.; Kitamura, M. In Modern Synthetic Methods 1989; Scheffold, R. Ed.; Springer-Verlag: Berlin, 1989; Vol. 5, p. 115.
8. (b) Narasaka, K. Synthesis 1991, 1.
9. (c) Whitesell, J. K. Chem. Rev. 1989, 89, 1581.
10. (a) Curran, D. P.; Qi, H. Y.; Geib, S. J.; DeMello, N. C. J. Am. Chem. Soc. 1994, 116, 3131.
11. (b) Curran, D. P.; DeMello, N. C. J. Chem. Soc., Chem. Commun. 1993, 1314.
12. (c) Qi, H. Ph.D. Thesis University of Pittsburgh, 1995. Barriers are estimated to be <25 kcal/mol.
13. (a) Hughes, A. D.; Price, D. A.; Shishkin, O.; Simpkins, N. S. Tetrahedron Lett. 1996, 37, 7607.
14. (b) Kitagawa, O.; Izawa, H.; Taguchi, T.; Shiro, M. Tetrahedron Lett. 1997, 38, 4447.
15. (c) DeMello, N. C. Ph.D. Thesis, University of Pittsburgh, 1995.
16. For a topical overview of these and related types of reactions, see: Clayden, J. Angew. Chem. Int. Ed. Eng. 1997, 36, 949.
17. Cass, Q. B.; Degani, A. L. G.; Tiritan, M. E.; Matlin, S. A.; Curran, D. P. Chirality 1997, 2, 9.
18. (a) Stewart, W. E.; Siddall, T. H., III Chem. Rev. 1970, 517.
19. (b) Oki, M. Top. Stereochem. Allinger, N. L.; Eliel, E. L.; Wiley, S. 1984, 14, 9-19.
20. (a) Pederson, B. F.; Pederson, B. Tetrahedron Lett. 1956, 2995-3001.
21. (b) Kessler, H.; Rieker, A. Liebigs Ann. Chem. 1967, 708, 57-68.
22. (c) Chupp, J. P.; Olin J. F. J. Org. Chem. 1967, 32, 2297-2301.
23. (a) Itai, A.; Toriumi, Y.; Saito, S.; Kagechika, H.; Shudo, K. J. Am. Chem. Soc. 1992, 114, 10649-10650.
24. (b) Azumaya, I.; Yamaguchi, K.; Kagechika, H.; Saito, S.; Itai, A.; Shudo, K. Yakugaku Zasshi 1994, 114, 414-430.
25. (c) Saito, S.; Toriumi, Y.; Tomioka, N.; Itai, A. J. Org. Chem. 1995, 60, 4715-4720.
26. (d) Azumaya, I.; Kagechika, H.; Yamaguchi, K.; Shudo, K. Tetrahedron 1995, 51, 5277-5290.
27. (e) Azumaya, I.; Yamaguchi, K.; Okamoto, I.; Kagechika, H.; Shudo, K. J. Am. Chem. Soc. 1995, 117, 9083-9084.
28. (a) Oki, M. In Applications of Dynamic NMR Spectroscopy to Organic Chemistry, VCH: Deerfield Beach. FL; 1985, 160-193.
29. (b) Price, B. J.; Eggleston, J. A.; Sutherland, I. O. J. Chem. Soc. (B) 1967, 922-925.
30. (c) Shvo, Y.; Taylor, E. C.; Mislow, K.; Raban, M. J. Am. Chem. Soc. 1967, 89, 4910-4917.
31. (d) Siddall, T. H., III; Stewart, W. E. J. Phys. Chem. 1969, 73, 40-45.
32. For representative crystal structures, see: (a) Pederson, B. F. Acta Chem. Scand. 1967, 21, 1415.
33. (b) Denne, W. A; Mackay, M. F. J. Cryst. Mol. Struct. 1974, 4, 141.
34. (c) Boeyens, J. C. A.; Denner, L.; Staskun, S. S. Afr. J. Chem. 1987, 40, 60.
35. (d) Wang, Q.-P.; Bennet, A. J.; Brown, R. S.; Santarsiero, B. D. J. Am. Chem. Soc. 1991, 113, 5757. See Ref. 11.
36. Porter, N. A.; Giese, B.; Curran, D. P. Acc. Chem. Res. 1991, 24, 296-304.
37. The shape of the Z-rotamer is reminiscent of 'sterically protected' esters. See: Suzuki, K.; Seebach, D. Liebigs Ann. Chem. 1992, 51.
38. Curran, D. P.; Heffner, T. A. J. Org. Chem. 1990, 55, 4585.
39. Reaction of methacrylamide 2e with t-butyl nitrile oxide provided a 1.5/1 mixture of stereoisomers whose relative configurations were not assigned. The major isomer existed in a 1/1 rotamer ratio and the minor isomer existed in a 2.5/1 rotamer ratio.
40. Dewar, M. J. S.; Zoebisch, E. F.; Healy, E. G.; Stewart, J. J. P. J. Am. Chem. Soc. 1985 107, 3902-3909. Calculations were conducted with the MOPAC 93.00 program, J. J. P. Stewart, Fujitsu Limited, Tokyo, Japan (1993). The molecular modelling was performed by the XMol program [Copyright @ 1991, 1992, 1993 by Research Equipment Inc. Minnesota Supercomputer Center, Inc.] Calculations were conducted on IBM Risc 6000 Workstation.
41. Dewar, M. J. S.; Zoebisch, E. F.; Healy, E. G.; Stewart, J. J. P. J. Am. Chem. Soc. 1985 107, 3902-3909. Calculations were conducted with the MOPAC 93.00 program, J. J. P. Stewart, Fujitsu Limited, Tokyo, Japan (1993). The molecular modelling was performed by the XMol program [Copyright @ 1991, 1992, 1993 by Research Equipment Inc. Minnesota Supercomputer Center, Inc.] Calculations were conducted on IBM Risc 6000 Workstation.
42. Myers, A. G.; Yang, B. H.; Chen, H.; McKinstry, L.; Kopecky, D. J.; Gleason, J. L. J. Am. Chem. Soc. 1997, 119, 6496-6511.
43. Pirkle, W.; Welch, C. J. Tetrahedron: Asymmetry 1994, 5, 777.
44. On several occasions, we succeeded in separating diastereomeric o-isopropyl benzanilides, only to have them re-equilibrate during the solvent evaporation stage. H. Yamada, unpublished observations.
45. Tiritan, M. E.; Cass, Q. B.; Del Alamo, A.; Matlin, S. A.; Grieb, S. J. Chirality, in press.
46. Matlin, S. A.; Tiritan, M. E.; Cass, Q. B.; Boyd, D. R. Chirality 1996, 8, 147.