Tetrahedron

Synthesis of β-and γ-hydroxy sulfones by regioselective opening of β, γ-epoxy sulfones

C Nájera, JM Sansano

Index: Najera, Carmen; Sansano, Jose Miguel Tetrahedron, 1990 , vol. 46, # 11 p. 3993 - 4002

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Citation Number: 15

Abstract

β, γ-Epoxy sulfones 1 derived from allylic sulfones react regio-selectively with organomagnesium compounds in the presence or not of catalytic amounts of copper (I) bromide to afford β-hydroxy sulfones 2 or γ-tosylated allylic alcoholates 5 respectively. The Michael type addition of Grignard reagents to intermediates 5 in the presence of catalytic amount of copper (l) bromide yields γ-hydroxy sulfones 6. The PCC oxidation of β-and γ- ...