Tetrahedron

Efficient intramolecular Diels–Alder reactions of ester-tethered 1, 7, 9-decatrienoates catalyzed by bis-aluminated trifluoromethanesulfonamide

A Saito, H Yanai, T Taguchi

Index: Saito, Akio; Yanai, Hikaru; Taguchi, Takeo Tetrahedron, 2004 , vol. 60, # 52 p. 12239 - 12247

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Citation Number: 23

Abstract

Recently we reported that the IMDA reaction of 1,7,9-decatrienoates can be efficiently promoted by a bidentate Lewis acid, in particular bis-aluminated trifluoromethane-sulfonamide generated in situ by mixing TfNH 2 (1 mol) and methylaluminum reagent (2 mol) (Eq. 1). 11 We assumed that coordination of both oxygen atoms of the ester group to a bidentate Lewis acid (possibly in equilibrium with other complex forms such as a double coordination form toward ...