Morifumi Fujita, Hiroshi Suzawa, T. Sugimura
May 12, 2008
Citations
0
Influential Citations
7
Citations
Journal
Tetrahedron Letters
Abstract
Reactions of pent-4-en-2-yl carboxylates and their derivatives with iodosylbenzene gave 2,4-disubstituted and 2,3,5-trisubstituted tetrahydrofurans with high diastereomeric ratio. The tetrahydrofuranylation may proceed via a 1,3-dioxan-2-yl cation intermediate generated by the participation of the internal acyloxy group in electrophilic attack of hypervalent iodine(III) toward acyloxyalkenes. Steric regulation owing to the cyclic structure of the cation accounts for the high stereoselectivity of the tetrahydrofuranylation.