Axial chirality in xanthene-4,5-dicarboxamides: 1,9-stereocontrol mediated by remote interactions between conformationally constrained amide groups

Tetrahedron Letters

Volumn 41, Issue 27, 2000, Pages 5171-5175

  Clayden, Jonathan ^a   Kenworthy, Martin N ^a   Youssef, Latifa H ^a   Helliwell, Madeleine ^a  

^a UNIVERSITY OF MANCHESTER   (United Kingdom)

Author keywords

[No Author keywords available]

Indexed keywords

ALKYL GROUP; DIAMIDE; LITHIUM DERIVATIVE; XANTHENE DERIVATIVE;

ALKYLATION; ARTICLE; CHEMICAL REACTION; CHIRALITY; CONFORMATION; DIASTEREOISOMER; ENANTIOMER; MOLECULAR INTERACTION; STEREOCHEMISTRY;

EID: 0034235916     PISSN: 00404039     EISSN: None     Source Type: Journal    
DOI: 10.1016/S0040-4039(00)00833-9     Document Type: Article

References (17)

1. Clayden, J.; Pink, J. H.; Yasin, S. A. Tetrahedron Lett. 1998, 39, 105.
2. Mills, R. J.; Taylor, N. J.; Snieckus, V. J. Org. Chem. 1989, 54, 4372.
3. Snieckus, V. Chem. Rev. 1990, 90, 879.
4. Clark, R. D.; Jahangir, A. Org. Reac. 1995, 47, 1.
5. Nowick, J. S.; Ballester, P.; Ebmeyer, F.; Rebek, J. J. Am. Chem. Soc. 1990, 112, 8902.
6. Hillebrand, S.; Bruckmann, J.; Krüger, C.; Haenel, M. W. Tetrahedron Lett. 1995, 36, 75.
7. Dierkes, P.; Ramdeehul, S.; Barloy, L.; De Cian, A.; Fischer, J.; Kamer, P. C. J.; Van Leeuwen, P. W. N. M.; Osborn, J. A. Angew. Chem., Int. Ed. Engl. 1998, 37, 3116.
8. McWilliams, K.; Kelly, J. W. J. Org. Chem. 1996, 61, 7408.
9. Bowles, P.; Clayden, J.; Helliwell, M.; McCarthy, C.; Tomkinson, M.; Westlund, N. J. Chem. Soc., Perkin Trans. 1 1997, 2607.
10. Ahmed, A.; Bragg, R. A.; Clayden, J.; Lai, L. W.; McCarthy, C.; Pink, J. H.; Westlund, N.; Yasin, S. A. Tetrahedron 1998, 54, 13277.
11. Pirkle, W. H.; Sikkenga, D. L.; Pavlin, M. S. J. Org. Chem. 1977, 42, 384.
12. Pirkle, W. H. Topics in Stereochemistry 1982, 13, 263.
13. This value was obtained using the approximation k=πΔν2 to estimate the rate of interconversion of enantiomers at the coalescence temperature of 80°C. See Ref. 10 and Sandström, J. Dynamic NMR Spectroscopy; Academic Press, London, 1982.
14. Clayden, J.; Pink, J. H. Tetrahedron Lett. 1997, 38, 2561.
15. Clayden, J.; Pink, J. H. Tetrahedron Lett. 1997, 38, 2565.
16. Clayden, J.; Westlund, N.; Wilson, F. X. Tetrahedron Lett. 1999, 40, 3331.
17. Clayden, J. Synlett 1998, 810.