Organic letters

Intramolecular Diels-Alder Reactions of Ester-Tethered 1, 7, 9-Decatrienoates: Bis [chloro (methyl) aluminum] trifluoromethanesulfonamide as a Catalyst

A Saito, H Ito, T Taguchi

Index: Saito, Akio; Ito, Hisanaka; Taguchi, Takeo Organic Letters, 2002 , vol. 4, # 26 p. 4619 - 4621

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Citation Number: 28

Abstract

The intramolecular Diels−Alder (IMDA) reaction is a powerful method for the stereocontrolled construction of functionalized cyclohexene frameworks. 2,3 In IMDA reactions, the nature of the tether linking the diene and dienophile strongly influences the reactivity of the substrate and the structure of the transition state, and thus the stereochemical outcome. Incorporation of an ester linkage in the tether often has a deleterious effect on the reaction. Even under the ...