A convenient and highly stereoselective method for synthesis of octahydropyrano[3,2-b]pyrrole derivatives

The octahydropyrano[3,2-b]pyrrole derivatives are synthesized by a double reductive amination from pyranose derivatives of nono-2,5-diuloses and octos-4-uloses and various amines. The cyclization proceeded smoothly in the presence of sodium triacetoxyborohydride to produce a series of novel fused N-heterobicyclic compounds with high stereoselectivity.

Graphical abstractFigure optionsDownload full-size imageDownload as PowerPoint slideHighlights► We have disclosed a mild, convenient and efficient method for the stereoselective synthesis of a series of octahydropyrano[3,2-b]pyrrole derivatives by using glycosyl-1,4-dicarbonyl compounds. ► A new approach to the octahydropyrano[3,2-b]pyrrole derivatives, which has undergone the double reductive amination in the presence of sodium triacetoxy-borohydride in dichloromethane at room temperature, was first reported.