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

Autor:	Hitomi Shimizu, Shigehiko Fukuda, Shimpei Sugiyama, Tsuyoshi Satoh
Rok vydání:	2009
Předmět:	Group (periodic table) Chemistry Organic Chemistry Electrophile medicine Medicinal chemistry Chloride Catalysis medicine.drug
Zdroj:	Synthesis. 2009:1323-1335
ISSN:	1437-210X 0039-7881
DOI:	10.1055/s-0028-1088019
Popis:	Treatment of γ- and δ-lactones having a sulfinyl group at the γ- and 5-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.
Databáze:	OpenAIRE
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