Diastereoselective synthesis of aryl and alkyl trans-glycidic amides from pseudoephedrine-derived sulfonium salt. Chemospecific exo-tet ring closure for morpholin-3-ones
作者： David M Aparicio , Dino Gnecco , Jorge R Juarez , Maria L Orea , Angel Mendoza
DOI: 10.1016/J.TET.2012.09.047
关键词: Alkyl 、 Stereochemistry 、 Sulfonium 、 Aryl 、 Carboxamide 、 Amide 、 Chemistry 、 Selectivity 、 Ring (chemistry) 、 Chemical synthesis
摘要: A regiospecific and high diastereoselective synthesis of trans-glycidic amides coming from a common pseudoephedrine sulfonium salt 2 precursor is presented. This the first example in where diastereoselectivity controlled by chiral noncyclic amide fragment. The epoxidation reaction provides alkyl or aryl glycidic good to excellent yields exclusive trans selectivity. Finally, through chemospecific 6-exo-tet ring closure trans-epoxyamides we access morpholin-3-ones densely functionalized with chemical stereochemical yields.
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