Stereoselective synthesis of 5-alkyliden-6-aminotetrahydro-2-pyranones through an unexpected isomerization of the hydroxytetrahydro-2-pyridinones obtained by the …

C Cimarelli, G Palmieri

Index: Cimarelli, Cristina; Palmieri, Gianni Tetrahedron, 1998 , vol. 54, # 5-6 p. 915 - 926

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Citation Number: 15

Abstract

A convenient methodology for the stereoselective preparation of 5-alkyliden-6- aminotetrahydro-2-pyranone 4 is reported. The synthesis of 2-pyranone 4 occurs through an unknown isomerization mechanism of the hydroxytetrahydro-2-pyridinone 3, an accessible starting material obtained by mild and selective reduction of the 5-acyltetrahydro-2- pyridinone 2. The isomerization mechanism and the stereoselectivity in the synthesis of 2- ...