107. - Jonathan Clayden

Communications
through ortho lithiation and electrophilic quenching (M. P. Sibi,
V. Snieckus, J. Org. Chem. 1983, 48, 1935). Full details will be
reported in a future publication.
[28] The decreased preference for the anti conformation in 5a in a
polar solvent (Table 1, entry 2) supports this explanation.
[29] CCDC 232753, 232754, and 232755 (5a, 5m, and 5s) contain the
supplementary crystallographic data for this paper. These data
can be obtained free of charge from The Cambridge Crystallographic
Data Centre via www.ccdc.cam.ac.uk/data_request/cif.
For an X-ray crystal structure indicating syn,syn stereochemistry
in a benzene-1,2,3-tricarboxamide, see: R. J. Mills, N. J. Taylor,
V. Snieckus, J. Org. Chem. 1989, 54, 4372.
[30] Molecular modeling studies were carried out using Macromodel
with the MM2* force field. See: F. Mohamadi, N. G. J. Richards,
W. C. Guida, R. Liskamp, M. Lipton, C. Caulfield, G. Chang, T.
Hendrickson, W. C. Still, J. Comput. Chem. 1990, 11, 440.
1244 2005 Wiley-VCH Verlag GmbH & Co. KGaA, Weinheim www.angewandte.org Angew. Chem. Int. Ed. 2005, 44, 1241 –1244