Conformational preference and remote (1,10) stereocontrol in biphenyl-2,2′-dicarboxamides

Organic Letters

Volumn 3, Issue 26, 2001, Pages 4133-4136

  Clayden, Jonathan ^a   Lund, Andrew ^a   Youssef, Latifa H ^a  

^a UNIVERSITY OF MANCHESTER   (United Kingdom)

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EID: 0042471847     PISSN: 15237060     EISSN: None     Source Type: Journal    
DOI: 10.1021/ol0167457     Document Type: Article

References (32)

1. (a) Bowles, P.; Clayden, J.; Helliwell, M.; McCarthy, C.; Tomkinson, M.; Westlund, N. J. Chem. Soc., Perkin Trans. 1 1997, 2607,
2. (b) Ahmed, A.; Bragg, R. A.; Clayden, J.; Lai, L. W.; McCarthy, C.; Pink, J. H.; Westlund, N.; Yasin, S. A. Tetrahedron 1998, 54, 13277.
3. (a) Clayden, J.; Lai, L. W. Angew. Chem., Int. Ed. 1999, 38, 2556.
4. (b) Clayden, J.; Johnson, P.; Pink, J. H.; Helliwell, M. J. Org. Chem. 2000, 65, 7033.
5. (c) Clayden, J.; Lai, L. W. Tetrahedron Lett. 2001, 42, 3163.
6. (a) Clayden, J.; Pink, J. H.; Yasin, S. A. Tetrahedron Lett. 1998, 39, 105.
7. (b) Clayden, J.; Kenworthy, M. N.; Youssef, L. H. Tetrahedron Lett. 2000, 41, 5171.
8. (c) Clayden, J.; Lai, L. W.; Helliwell, M. Tetrahedron: Asymmetry 2001, 12, 695.
9. Clayden, J.; Westlund, N.; Wilson, F. X. Tetrahedron Lett. 1999, 40, 3331.
10. Below -20 °C, decoalescences occur as a result of slow Ar-Ar rotation. Rotation of the conformer shown in Figure 1 about the Ar-Ar axis is an enantiomerization and would interconvert the signals of the two rings.
11. (a) Mills, R. J.; Horvath, R. F.; Sibi, M. P.; Snieckus, V. Tetrahedron Lett. 1985, 26, 1145.
12. (b) Snieckus, V. Chem. Rev. 1990, 90, 879.
13. For a related case, see ref 4.
14. (a) Adams, R.; Yuan, H. C. Chem. Rev. 1933, 12, 261.
15. (b) Eliel, E. L.; Wilen, S. H. Stereochemistry of Organic Compounds; Wiley: New York, 1994.
16. Whelk-O1 from Regis.
17. 2-3a - f the highest field methyl doublet lies between δ 0.80 and 0.90.
18. Mills, R. J.; Taylor, N. J.; Snieckus, V. J. Org. Chem. 1989, 54, 4372.
19. (a) Clayden, J.; Pink, J. H. Tetrahedron Lett. 1997, 38, 2565.
20. (b) Clayden, J.; Pink, J. H. Tetrahedron Lett. 1997, 38, 2565.
21. (c) Clayden, J.; Helliwell, M.; Pink, J. H.; Westlund, N. J. Am. Chem. Soc. in press.
22. (d) Clayden, J.; Darbyshire, M.; Pink, J. H.; Westlund, N.; Wilson, F. X. Tetrahedron Lett. 1997, 38, 8587.
23. (a) Clayden, J.; Westlund, N.; Wilson, F. X. Tetrahedron Lett. 1996, 37, 5577.
24. (b) Clayden, J.; Westlund, N.; Wilson, F. X. Tetrahedron Lett. 1999, 40, 7883.
25. (c) Clayden, J.; Westlund, N.; Wilson, F. X. Tetrahedron Lett. 1999, 40, 3329.
26. (d) Clayden, J.; Westlund, N.; Beddoes, R. L.; Helliwell, M. J. Chem. Soc., Perkin Trans. 1 2000, 1351.
27. (e) Clayden, J.; McCarthy, C.; Westlund, N.; Frampton, C. S. J. Chem. Soc., Perkin Trans. 1 2000 1363.
28. (f) Clayden, J.; Westlund, N.; Frampton, C. S. J. Chem. Soc., Perkin Trans. 1 2000, 1379.
29. For an example of remote stereochemical control around rigid ring-systems mediated by amides, see ref 3.
30. 1H NMR spectrum of the crude product from 9and PhMgBr with that from the reaction of 9 with PhLi (which gives a 2:1 ratio of diastereoisomers in 94% yield) indicated a stereoselectivity of >20:1. The stereochemistry of 10 is assigned tentatively by analogy additions to 2-formyl naphthamides (see ref 13a,e).
31. Pellón, R. F.; Carrasco, R.; Milián, V.; Rodés, L. Synth. Commun. 1995, 25, 1077.
32. Shapiro, R.; Slobodin, D. J. Org. Chem. 1969, 34, 1165.