Stereoselective synthesis of tetrahydropyran-4-ones from dioxinones catalyzed by scandium (III) triflate

WJ Morris, DW Custar, KA Scheidt

Index: Morris, William J.; Custar, Daniel W.; Scheidt, Karl A. Organic Letters, 2005 , vol. 7, # 6 p. 1113 - 1116

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Citation Number: 41

Abstract

A scandium triflate catalyzed, diastereoselective cyclization between aldehydes and β- hydroxy dioxinones has been discovered. This process capitalizes on the untapped nucleophilicity of the embedded enol ether within the dioxinone core. The bicyclic compounds from the resulting cyclization can be isolated, or alternatively, alkoxide nucleophiles can be directly added. This in situ addition fragments the dioxinone rings ...