Synthesis of Some Selectively <i>N</i>-Protected (1<i>S</i>,2<i>S</i>)-<i>p</i>-Nitrophenylserinol–Based Diamino-1,3-dioxanes and Tripodands
收藏资源简介：
The unconventional methodology for the non-epimerisable cycloacetalization of optically active (1<i>S</i>,2<i>S</i>)-2-amino-1-(4-nitrophenyl)propane-1,3-diol (<i>p-nitrophenylserinol</i>) (concd. H<sub>2</sub>SO<sub>4</sub> 96% as solvent and catalyst, <i>i.e., sulphuric transacetalization</i>) producing (2<i>R</i>,4<i>S</i>,5<i>S</i>) diamino-1,3-dioxanes, was enlarged by the use of <i>N</i>-protected forms of 2,2-DiMethoxyEthylAmine (DMEA, aminoacetaldehyde dimethylacetal). Conversely, <i>N</i>-protected derivatives of <i>p</i>-nitrophenylserinol were successfully cyclocondensed with DMEA in the same sulphuric conditions. <i>N</i>-functionalization of DMEA upon treatment with trimesic acid trichloride and cyanuric chloride yielded the corresponding triple amide and melamine respectively. Their adapted sulphuric transacetalization in triplicate in reaction with <i>arylserinols</i> (aryl: phenyl, <i>p</i>-nitrophenyl) afforded a new series of optically active tripodands.
