Chemistry Letters

A Direct Synthesis of γ-, δ-, and ε-Lactones Utilizing SmI 2-induced Barbier-type Reaction in the Presence of Hexamethylphosphoric Triamide (HMPA)

K Otsubo, K Kawamura, J Inanaga, M Yamaguchi

Index: Otsubo, Kenji; Kawamura, Kisa; Inanaga, Junji; Yamaguchi, Masaru Chemistry Letters, 1987 , p. 1487 - 1490

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Citation Number: 57

Abstract

By using an efficient reduction system of SmI 2-THF-HMPA, the coupling reaction of β-, γ, or δ-bromoesters with carbonyl compounds was completed within a minute at room temperature affording γ-, δ-, or ε-lactones, respectively, in good yields. Cp 2 ZrCl 2 was also found to be effective for the coupling with ketones.