Tetrahedron Letters

Tin (IV) triflimidate-catalyzed cyclization of epoxy esters to functionalized δ-hydroxy-γ-lactones

S Antoniotti, E Duñach

Index: Antoniotti, Sylvain; Dunach, Elisabet Tetrahedron Letters, 2009 , vol. 50, # 21 p. 2536 - 2539

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Citation Number: 20

Abstract

In the presence of 5mol% of tin (IV) triflimidate, a cyclization reaction of epoxyesters to δ- hydroxy-γ-lactones proceeding in 46–98% yields without additives, ligands, or co-catalysts was observed. The cyclization to five-membered rings is greatly favored compared to the possible six-membered rings formation and is probably under the control of a Thorpe–Ingold type effect.