Abstract
| - The synthesis and reactivity study of a first generation serineprotease mimic is described. Centralin the design stands the possibility of stabilization of the transitionstate by an amino triol such as8t. En route to 8t, a series of aminoalcohols (4−8) was obtained, the reactivity ofwhich wasstudied toward esterification by acetylimidazole (AcIm) and byp-nitro-2,2,2-trifluoroacetanilide(PNTFA). Interesting reactivity differences were observed betweenthe cis- and the trans-series,especially between 7c and 7t (AcIm), and between8c and 8t (PNTFA). In both cases theresultsare explained by invoking extra stabilization of the tetrahedraloxyanion.
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