Tetrahedron letters

Stereoselective synthesis of 1, 4-dienes by chelation-controlled reduction of benzothiazole β-oxosulfides

V Caló, A Nacci

文献索引：Calo, Vincenzo; Nacci, Angelo Tetrahedron Letters, 1998 , vol. 39, # 22 p. 3825 - 3828

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被引用次数: 5

摘要

Allylated β-oxosulfides of benzothiazole can replace β-oxophosphane oxides to provide a stereospecific alkene synthesis. These sulfides, by reduction with sodium borohydride afford predominantly syn β-hydroxy sulfides. DIBAL reduction in the presence of magnesium bromide improves the syn stereomer formation. Base treatment of these β-hydroxy sulfides affords (Z)-allyl thiiranes which are converted into (E, Z)-dienes.