Conjugate addition of lithium ester enolates to 1-chlorovinyl p-tolyl sulfoxides: a novel synthesis of functionalized esters and lactones having a tertiary or a quaternary carbon at the β-position

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• 作者：Satoh ; Tsuyoshi ; Sugiyama ; Shimpei ; Kamide ; Yuhki ; Ota ; Hiroyuki
• 关键词：carboxylic acid ; spiro-lactone ; α ; -methylene γ ; -lactone ; quaternary carbon ; sulfoxide
• 刊名：Tetrahedron
• 出版年：2003
• 出版时间：June 9, 2003
• 年：2003
• 卷：59
• 期：24
• 页码：4327-4336
• 全文大小：258 K

文摘

Addition of the lithium ester enolates to 1-chlorovinyl p-tolyl sulfoxides, which were synthesized from chloromethyl p-tolyl sulfoxide and ketones or aldehydes, gave esters having a tertiary or a quaternary carbon at the 3-position, and chlorine and sulfinyl groups at the 4-position in high to quantitative yields. The adducts were converted to various esters having methyl, formyl, and hydroxycarbonyl groups at the 3-position. A novel method for the synthesis of γ-lactones, including spiro-type γ-lactones and α-methylene γ-lactones, was realized from the adducts in good overall yields. The scope and limitations of this method and the mechanism of the reactions are also discussed.