Study On Synthesis Of Amino - O - Diamine And Its Derivatives

Aryl vicinal diamines are very important motifs which have been broadlyemployed as key functional elements in various bioactive compounds and numerouspowerful catalysts.Although the students of aryl vicinal diamines have attracted much attention inorganic chemistry commonly, the development of new synthetic method for arylvicinal diamines is still highly desirable.a-Amino anions are useful intermediates, which can react with variouselectrophiles to access various amines. However, it is not easy to obtain a-aminoanions under mild conditions. Very recently we developed an efficient method forgenerating delocalized a-imino anions by decarboxylation of lithium salts of2，2-diphenylglycinate imines in aprotic solvent THF. The Schiff base lithium saltscould be obtained from electrophilic aldehydes via condensation with lithium2，2-diphenylglycinate in methanol. When imines are used as the electrophiles, thevicinal diamines will be obtained from the a-amino anions.The transformation not only builds a new C-C bond，but also forms a new C-Nbond, providing a new strategy and method to access aryl vicinal alkamines andvicinal diamines. Our work mainly includes the following three parts:1.A series of Schiff base compounds were prepared by the reaction of differentaromatic aldehydes and/?-toluenesulfonamide. The lithium salts of2,2-diphenyl-glycinate imines were also prepared by the reaction of benzaldehyde, lithium/er/-butoxide and2,2-di°phenylglycine at20C in methanol.2.Optimization of reaction conditions including solvent, reaction temperature,additive, additive loading, reaction time and so on, were carried out for thetransformtion.3.Substrate scope for transformation was examinated under the optimizedconditions.