A novel biomimetic condensation of 2-deoxyribose, aryl amine and acetyl acetone to bicyclic aminols catalyzed by InCl3

2-Deoxyribose, an aryl amine and acetyl acetone undergo smooth cyclocondensation in the presence of 10 mol % of InCl3 under mild conditions to afford the corresponding sugar-derived bicyclic aminols in good yields with moderate diastereoselectivity. This reaction is reminiscent of the celebrated tropinone synthesis of Robinson. The structures of the products are established by using various NMR experiments and X-ray crystallographic studies.

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