Tetrahedron letters

The first example of γ-chloromagnesio γ-lactones: their generation from γ-tolylsulfinyl γ-lactones with isopropylmagnesium chloride, stability, and reaction with …

S Sugiyama, H Shimizu, T Satoh

Index: Sugiyama, Shimpei; Shimizu, Hitomi; Satoh, Tsuyoshi Tetrahedron Letters, 2006 , vol. 47, # 49 p. 8771 - 8775

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Citation Number: 16

Abstract

The treatment of γ-lactones having a sulfinyl group at the γ-position, which were synthesized from 1-chlorovinyl p-tolyl sulfoxides with lithium enolate of carboxylic esters, with isopropyl magnesium chloride in THF at− 78° C gave γ-chloromagnesio γ-lactones by the sulfoxide– magnesium exchange reaction in high yields. The generated γ-chloromagnesio γ-lactones were found to be stable at below− 50° C for at least 2h. The reaction of these γ- ...