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Synthesis 2009(8): 1323-1335  
DOI: 10.1055/s-0028-1088019
PAPER
© Georg Thieme Verlag Stuttgart ˙ New York

γ-Chloromagnesio γ-Lactones and δ-Chloromagnesio δ-Lactones: Generation, Properties, and Synthetic Uses

Hitomi Shimizu, Shigehiko Fukuda, Shimpei Sugiyama*, Tsuyoshi Satoh
Department of Chemistry, Faculty of Science, Tokyo University of Science, Ichigaya-Funagawara-machi, Shinjuku-ku, Tokyo 162-0826, Japan
Fax: +81(565)52614631; e-Mail: ssugi@rs.kagu.tus.ac.jp;
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Publikationsverlauf

Received 26 November 2008
Publikationsdatum:
16. März 2009 (online)

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Abstract

Treatment of γ- and δ-lactones having a sulfinyl group at the γ- and δ-positions with isopropylmagnesium chloride in THF at -78 ˚C gave γ-chloromagnesio γ-lactones and δ-chloromagnesio δ-lactones, respectively, by the sulfoxide-magnesium exchange reaction in high yields. Comparing the stability of the γ-chloromagnesio γ-lactones with that of the δ-chloromagnesio δ-lactones, the former was found to be much more stable. The reaction of these γ-chloromagnesio γ-lactones and δ-chloromagnesio δ-lactones with electrophiles and the stereochemistry of the reactions are discussed.

Key words

γ-chloromagnesio γ-lactone - δ-chloromagnesio δ-lactone - sulfoxide-magnesium exchange reaction - organomagnesium compound - Grignard reagent

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