Tetrahedron

Anion reaction of 1, 3-benzoxathiole-3-oxide with several electrophilic compounds

…, S Melis, G Gelli, MG Cabiddu, C Fattuoni, S De Montis…

Index: Cabiddu, Salvatore; Cadoni, Enzo; Melis, Stefana; Gelli, Gioanna; Grazia Cabiddu, Maria; Fattuoni, Claudia; De Montis, Stefania; Ianelli, Sandra Tetrahedron, 2001 , vol. 57, # 52 p. 10365 - 10375

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Citation Number: 7

Abstract

The reaction of benzoxathiole-3-oxide with LDA in THF or THF/hexane or THF/HMPA gave a carbanion which was reacted with methyl iodide, aromatic aldehydes or carbon dioxide. The conformational stability (α-diastereoselectivity) of the carbanion and the asymmetric induction due to the prochiral electrophiles (β-diastereoselectivity) was studied. The temperature and the solvent effects on the α-and β-diastereoselectivity are discussed.