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Reversal of diastereoselectivity in the synthesis of Peptidomimetic 3‑Carboxamide-1,4-benzodiazepin-5-ones
Organic Letters. 2015, V. 17, n. 3, p. 612–615
American Chemical Society
Fecha de publicación
Enantiopure 3-carboxamide-1,4-benzodiazepin-5-ones were synthesized via the Ugi reaction followed by the Staudinger/aza-Wittig or reduction reactions in only two steps. A complete reversal of diastereoselectivity was achieved depending on the cyclization methodology employed. The different orientation of the C3 substituent in our 3-substituted 1,4-benzodiazepin-5-ones with respect to the most studied 1,4-benzodiazepin-2-ones makes them complementary in the development of new drugs because the primary source of binding selectivity of 1,4-benzodiazepines is the selective recognition of ligand conformations by the receptor.
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