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A highly enantioselective synthesis of 2,6-disubstituted atropisomeric anilides through enantiotopic selective lithiation of a prochiral 2,6-disubstituted arene chromium complex with stoichiometric chiral base was recently reported by Uemura et al. However, this method cannot be applied to the synthesis of atropisomeric o-tert-butylanilide which can effectively work as a chiral molecule. (a) Hata, T.; Koide, H.; Taniguchi, N.; Uemura, M. Org. Lett. 2000, 2, 1907.
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N,N-Dialkyl 2,6-disubstituted aromatic amides are also known to exist as stable nonbiaryl atropisomeric compounds at room temperature. Recently, the stereoselective synthesis of optically active forms of these compounds has been reported by several groups. (a) Thayumanavan, S.; Beak, P.; Curran, D. P.; Tetrahedron Lett. 1996, 37, 2899.
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