A straightforward synthesis of an aminocyclitol based on an enzymatic aldol reaction and a highly stereoselective intramolecular Henry reaction

L El Blidi, D Crestia, E Gallienne, C Demuynck…

文献索引：El Blidi, Lahssen; Crestia, Dominique; Gallienne, Estelle; Demuynck, Colette; Bolte, Jean; Lemaire, Marielle Tetrahedron Asymmetry, 2004 , vol. 15, # 18 p. 2951 - 2954

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被引用次数: 40

摘要

The reactions of 4-nitroaldehydes 9 and 10 with dihydroxyacetonephosphate (DHAP) catalyzed by fructose-1, 6-diphosphate aldolase from rabbit muscle were studied. Starting from 9 or 10, only one main stereomer of nitrocyclitol 8 was isolated. A highly stereoselective intramolecular cyclization (Henry reaction or nitroaldol reaction) took place under acidic conditions during the aldolase catalyzed condensation and phytase catalyzed phosphate ...