Atropisomeric diastereoisomers from nucleophilic attack on 8-acyl-1-naphthamides

Journal of the Chemical Society, Perkin Transactions 1

Volumn , Issue 9, 2000, Pages 1379-1385

  Clayden, Jonathan ^a,b   Westlund, Neil ^a,b   Frampton, Christopher S ^a,b  

^a UNIVERSITY OF MANCHESTER   (United Kingdom)

^b ROCHE PRODUCTS LTD   (United Kingdom)

Author keywords

[No Author keywords available]

Indexed keywords

ALCOHOLS; ISOMERS; MOLECULAR ORIENTATION; THERMODYNAMICS;

NUCLEOPHILES;

STEREOCHEMISTRY;

EID: 0034616480     PISSN: 14704358     EISSN: None     Source Type: Journal    
DOI: 10.1039/b000670j     Document Type: Article

References (44)

1. See the two preceding papers: J. Clayden, N. Westlund, R. L. Beddoes and M. Helliwell, J. Chem. Soc., Perkin Trans, 1, 2000, DOI: 10.1039/b000668h;
2. J. Clayden, C. McCarthy, N. Westlund and C. S. Frarapton, J. Chem. Soc., Perkin Trans. 1,2000, DOI: 10.1039/ b000669f.
3. Preliminary communication: J. Clayden, N. Westlund and F. X. Wilson, Tetrahedron Lett., 1999, 40, 7883.
4. K. Fuji, T. Kawabata, A. Kuroda and T. Taga, J. Org. Chem., 1995, 60, 1914.
5. K. Fuji, X.-S. Yang, K. Tanaka, N. Asakawa and X.-J. Hao, Tetrahedron Lett., 1996, 37, 7373.
6. K. Fuji and T. Kawabata, Tetrahedron Lett., 1998, 39, 6323.
7. A. S. Cooke and M. M. Harris, J. Chem. Soc., 1963, 2365.
8. Y. Badar, A. S. Cooke and M. M. Harris, J. Chem. Soc., 1965, 1412.
9. M. M. Harris, R. Z. Mazcngo and A. S. Cooke, J. Chem. Soc. (C), 1967, 2575.
10. A. S. Cooke and M. M. Harris, J. Chem. Soc. (C), 1967, 988.
11. A. I. Meyers and M. J. McKennon, Tetrahedron Lett., 1995, 36, 5869.
12. K. Fuji, M. Sakurai, N. Tohkai, A. Kuroda, T. Kawabata, Y. Fukuzawa, T. Kinoshita and T. Tada, Chem. Commun., 1996, 1609.
13. A. Ahmed, R. A. Bragg, J. Clayden, L. W. Lai, C. McCarthy, J. H. Pink, N. Westlund and S. A. Yasin, Tetrahedron, 1998, 54, 13277.
14. R. J. Clouah and J. B. Roberts, J. Am. Chem. Soc., 1976, 98, 1018.
15. H. O. House and R. W. Bashe, J. Org. Chem., 1965, 30, 2942.
16. H. O. House, W. J. Campbell and M. Gall, J. Org. Chem., 1970, 35, 1815.
17. J. M. Zoltewicz, N. M. Maier and W. M. F. Fabian, J. Org. Chem., 1996, 61, 7018.
18. J. A. Zoltewicz, N. Maier and W. M. F. Fabian, Tetrahedron, 1996, 52, 8703.
19. J. A. Zoltewicz, N. Maier and W. M. F. Fabian, J. Org. Chem., 1998, 63, 4985.
20. S. B. Bulgarevich, N. A. Ivanova, D. Y. Movshovich, A. Mannschreck, L. Kiessl, H. Zinner and C. Kiefl, J. Mol. Struct., 1992, 265, 417.
21. S. B. Bulgarevich, N. A. Ivanova, D. Y. Movshovich, A. Mannschreck and C. Kiefl, J. Mol. Struct., 1994, 326, 17.
22. A. Mannschreck, H. Zinner and N. Pustet, Chimia, 1989, 43, 165.
23. C. Kiefl and A. Mannschreck, Synthesis, 1995, 1033.
24. A. J. Birch, M. Salahud-Din and D. C. C. Smith, J. Chem. Soc. (C), 1966, 523.
25. J. Clayden, C. S. Frampton, C. McCarthy and N. Westlund, Tetrahedron, 1999, 55, 14161.
26. R. L. Gay and C. R. Hauser, J. Am. Chem. Soc., 1967, 89, 2297.
27. J. Clayden, C. McCarthy and M. Helliwell, Chem. Commun., 1999, 2059.
28. A. I. Meyers and A. Price, J. Org. Chem., 1998, 412.
29. J. P. H. Charmant, G. C. Lloyd Jones, T. M. Peakman and R. L. Woodward, Tetrahedron Lett., 1998, 39, 4233.
30. R. W. Alder, Chem. Rev., 1989, 89, 1215.
31. T. Fujii, H. Sakuragi and N. Furukawa, Tetrahedron Lett., 1995, 36, 8039.
32. W. Nakanishi, S. Hayashi and S. Toyota, J. Org. Chem., 1998, 63, 8790.
33. J. Handal, J. G. White, R. W. Franck, Y. H. Yuh and N. L. Allinger, J. Am. Chem. Soc., 1977, 99, 3345.
34. A. J. Kirby and J. M. Percy, Tetrahedron, 1988, 44, 6911.
35. J. V. Popovici-Müller and T. A. Spencer, Tetrahedron Lett., 1997, 38, 8161.
36. A. J. Kirby and J. M. Percy, Tetrahedron, 1988, 44, 6903.
37. W. B. Schweizer, G. Procter, M. Kaftory and J. D. Dunitz, Heh: Chim. Acta, 1978, 61, 2783.
38. R. H. Mitchell, T. K. Vinod and G. W. Bushell, J. Am. Chem. Soc., 1990, 112, 3847.
39. F. Cozzi, M. Cinquini, R. Annunziata and J. S. Siegel, J. Am. Chem. Soc., 1993, 115, 5330.
40. A. Bahl, W. Grahn, S. Stadler, F. Feiner, G. Bowhill, C. Bräuchte, A. Reisner and P. G. Jones, Angew. Chem., Int. Ed. Engt., 1995, 34, 1485.
41. J. Clayden, N. Westlund and F. X. Wilson, Tetrahedron Lett., 1996, 37, 5577.
42. M. Watanabe and V. Snieckus, J. Am. Chem. Soc., 1980, 102, 1457.
43. SMART, SAINT and SADABS area-detector control and integration software, Bruker AXS Inc., Madison, WI 53719, USA, 1997.
44. G. M. Sheldrick. SHELXTL, Bruker AXS Inc., Madison, WI 53719, USA, 1997.