The addition of primary and secondary aliphatic amines to glycal-derived allyl epoxides is completely 1,2-regio- and anti-stereoselective, whereas mixtures of the corresponding anti-1,2- [3–N-(substituted-amino) glycals] and anti-1,4-addition products (N-glycosyl amines) are obtained with N-(mesyl)-aziridines. In this way, structural moieties, otherwise difficult to synthesize, are obtained by means of a very simple protocol. The regio- and stereoselectivity observed with epoxides is the consequence of an isomerization process, whereas the result obtained with aziridines is explained by the absence of an effective substrate–nucleophile (amine) coordination.
|Autori:||V. DI BUSSOLO; L. FAVERO; M. PINESCHI; P. CROTTI; L. CHECCHIA; M. R. ROMANO|
|Titolo:||Aminolysis of Glycal-Derived Allyl Epoxides and Activated Aziridines. Effects of the Absence of Coordination Processes on the Regio- and Stereoselectivity,|
|Anno del prodotto:||2010|
|Digital Object Identifier (DOI):||10.1016/j.tet.2009.11.059|
|Appare nelle tipologie:||1.1 Articolo in rivista|