Stereocontrol with rotationally restricted amides

Synlett

Volumn , Issue 8, 1998, Pages 810-816

  Clayden, Jonathan ^a  

^a UNIVERSITY OF MANCHESTER   (United Kingdom)

Author keywords

[No Author keywords available]

Indexed keywords

EID: 0002046801     PISSN: 09365214     EISSN: None     Source Type: Journal    
DOI: 10.1055/s-1998-1784     Document Type: Article

References (35)

1. Clayden, J.; Cooney, J. J. A.; Julia, M. J. Chem. Soc., Perkin Trans. 1 1995, 7.
2. Bedford, G. R.; Greatbanks, D.; Rogers, D. B. J. Chem. Soc., Chem. Commun. 1966, 330.
3. Lewin, A. H.; Frucht, M. Tetrahedron Lett. 1970, 1079.
4. Fulea, A. O.; Krueger, P. J. Tetrahedron Lett. 1975, 3135.
5. Siddall, T. H.; Garner, R. H. Can. J. Chem. 1966, 44, 2387.
6. Ackerman, J. H.; Laidlaw, G. M.; Snyder, G. A. Tetrahedron Lett. 1969, 3879.
7. Jennings, W. B.; Tolley, M. S. Tetrahedron Lett. 1976, 695.
8. Berg, U.; Sandström, J. Tetrahedron Lett. 1976, 3197.
9. Cuyegkeng, M. A.; Mannschreck, A. Chem. Ber. 1987, 120, 803.
10. Pirkle, W. H.; Welch, C. J.; Zych, A. J. J. Chromatography 1993, 648, 101.
11. Gasparrini, F.; Misiti, D.; Pierini, M.; Villani, C. Tetrahedron Asymmetry 1997, 8, 2069.
12. Clayden, J. Angew. Chem., Int. Ed. Engl. 1997, 35, 949.
13. Curran, D. P.; Qi, H.; Geib, S. J.; DeMello, N. C. J. Am. Chem. Soc. 1994, 116, 3131.
14. Hughes, A. D.; Price, D. A.; Shishkin, O.; Simpkins, N. S. Tetrahedron Lett. 1996, 37, 7607.
15. Kitagawa, O.; Izawa, H.; Taguchi, T.; Shiro, M. Tetrahedron Lett. 1997, 38, 4447.
16. Bowles, P.; Clayden, J.; Tomkinson, M. Tetrahedron Lett. 1995, 56, 9219.
17. Bowles, P.; Clayden, J.; Helliwell, M.; McCarthy, C.; Tomkinson, M.; Westlund, N. J. Chem. Soc., Perkin Trans. I 1997, 2607.
18. Stewart, W. H.; Siddall, T. H. Chem. Rev. 1970, 70, 517.
19. Sandström, J. Dynamic NMR Spectroscopy; Academic Press: London, 1982.
20. Ahmed, A.; Bragg, R. A.; Clayden, J.; Lai, L. W.; McCarthy, C.; Pink, J. H.; Westlund, N.; Yasin, S. A. manuscript in preparation.
21. Our investigations of the barriers to rotation about the chiral axis of tertiary aromatic amides will be published shortly.
22. Clayden, J.; Darbyshire, M.; Pink, J. H.; Westlund, N.; Wilson, F. X. Tetrahedron Lett. 1997, 38, 8487.
23. Clayden, J.; Westlund, N.; Wilson, F. X. Tetrahedron Lett. 1996, 37, 5577.
24. Thayumanavan, S.; Lee, S.; Liu, C.; Beak, P. J. Am. Chem. Soc. 1994, 116, 9755.
25. Thayumanavan, S.; Beak, P.; Curran, D. P. Tetrahedron Lett. 1996, 37, 2899.
26. Clayden, J.; Pink, J. H. Tetrahedron Lett. 1997, 38, 2561.
27. Beak, P.; Tse, A.; Hawkins, J.; Chen, C. W.; Mills, S. Tetrahedron 1983, 59, 1983.
28. Beak, P.; Basu, A.; Gallagher, D. J.; Park, Y. S.; Thayumanavan, S. Acc. Chem. Res. 1996, 29, 552.
29. Clayden, J.; Pink, J. H. Tetrahedron Lett. 1997, 38, 2565.
30. Reich, H. J.; Borst, J. P.; Coplien, M. B.; Phillips, N. H. J. Am. Chem. Soc. 1992, 114, 6577. I am grateful to Prof Reich, and also to Prof R W Hoffmann, for communicating their insights on the poor stereospecificity of our reaction.
31. Still, W. C.; Sreekumar, C. J. Am. Chem. Soc. 1980, 102, 1201.
32. Carstens, A.; Hoppe, D. Tetrahedron 1994, 50, 6097.
33. Hoppe, D.; Paetow, M.; Hintze, F. Angew. Chem., Int. Ed. Engl. 1993, 52, 394.
34. Mills, R. J.; Taylor, N. J.; Snieckus, V. J. Org. Chem. 1989, 54, 4372.
35. Ahmed, A.; Clayden, J.; Rowley, M. J. Chem. Soc., Chem. Commun. 1998, 297.