Aminolysis of glycal-derived allyl epoxides and activated aziridines. Effects of the absence of coordination processes on the regio- and stereoselectivity

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• 作者：Valeria Di Bussolo ; Lorenzo Checchia ; Maria Rosaria Romano ; Lucilla Favero ; Mauro Pineschi ; Paolo Crotti
• 关键词：Glycals ; Allyl epoxides ; Allyl aziridines ; Aminolysis
• 刊名：Tetrahedron
• 出版年：2010
• 出版时间：16 January 2010
• 年：2010
• 卷：66
• 期：3
• 页码：689-697
• 全文大小：592 K

文摘

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.