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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

✍ Scribed by Tsuyoshi Satoh; Shimpei Sugiyama; Yuhki Kamide; Hiroyuki Ota

Publisher
Elsevier Science
Year
2003
Tongue
French
Weight
258 KB
Volume
59
Category
Article
ISSN
0040-4020

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✦ Synopsis

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 g-lactones, including spiro-type g-lactones and a-methylene g-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.

📜 SIMILAR VOLUMES

A novel synthesis of carboxylic acid der
A novel synthesis of carboxylic acid derivatives having a quaternary carbon at 3-position and functional groups at 4-position from 1-chlorovinyl p-tolyl sulfoxides and acetic acid esters
✍ Tsuyoshi Satoh; Shimpei Sugiyama; Hiroyuki Ota 📂 Article 📅 2002 🏛 Elsevier Science 🌐 French ⚖ 112 KB

Addition of the lithium enolate of acetic acid esters to 1-chlorovinyl p-tolyl sulfoxides, which were derived from ketones and chloromethyl p-tolyl sulfoxide in three steps in good yields, gave carboxylic acid esters having a quaternary carbon at the 3-position, and chlorine and sulfinyl groups at t