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.
Aminolysis of Glycal-Derived Allyl Epoxides and Activated Aziridines. Effects of the Absence of Coordination Processes on the Regio- and Stereoselectivity,
DI BUSSOLO, VALERIA;FAVERO, LUCILLA;PINESCHI, MAURO;CROTTI, PAOLO;
2010-01-01
Abstract
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.I documenti in IRIS sono protetti da copyright e tutti i diritti sono riservati, salvo diversa indicazione.