Record number :
1087642
Title of article :
Studies on the stereoselective selenolactonization, hydroxy and methoxy selenenylation of α- and β-hydroxy acids and esters. Synthesis of δ- and γ-lactones
Author/Authors :
Carmela Aprile، نويسنده , , Michelangelo Gruttadauria، نويسنده , , Maria E Amato، نويسنده , , Francesca DʹAnna، نويسنده , , Paolo Lo Meo، نويسنده , , Serena Riela، نويسنده , , Renato Noto، نويسنده ,
Issue Information :
هفته نامه با شماره پیاپی سال 2003
Pages :
11
From page :
2241
To page :
2251
Abstract :
The diastereoselective synthesis of hydroxy substituted γ- and δ-lactones was accomplished following two approaches. A 5- or 6-endo cyclization promoted by electrophilic selenium reagents of α- or β-hydroxy acids and a 5- or 6-exo cyclization of hydroxy esters obtained through a diastereoselective hydroxy selenenylation reaction of α- or β-hydroxy esters. Moreover, the diastereoselective methoxy selenenylation of the above compounds was investigated showing a case in which the compound that was unreactive in the hydroxy selenenylation conditions gave, in the methoxy selenenylation conditions, the deprotected diol. The usefulness of the methoxy selenenylation procedure was proven by the preparation of a symmetric compound unsymmetrically functionalized. Yields and selectivities were found to depend on substituents (Ph or alkyl groups at the carbon atom that undergoes the nucleophilic attack), mode of cyclization, kinetic or thermodynamic control conditions. In the latter case, silica gel played an important role.
Keywords :
Diols , Lactones , Cyclization , selenium and compounds
Journal title :
Tetrahedron
Serial Year :
2003
Link To Document :
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