One-carbon ring-expansion of 2-substituted cyclohexanones via lithium- and magnesium β-oxido carbenoid rearrangement: a new synthesis of 2,7-disubstituted and 2,2,7-trisubstituted cycloheptanones

Tsuyoshi Satoh*, Shu Tanaka, Naoyuki Asakawa

*この研究の対応する著者

研究成果: Article査読

11 被引用数 (Scopus)

抄録

Lithium α-sulfinyl carbanion of 1-chloroethyl p-tolyl sulfoxide was reacted with 2-substituted cyclohexanones to afford adducts in good yields. The adducts were treated with LDA or t-BuMgCl to give lithium or magnesium alkoxides, which were treated with t-BuLi or i-PrMgCl to afford one-carbon ring-expanded 2,7-disubstituted cycloheptanones through β-oxido carbenoids. Interestingly, 2,3-disubstituted cycloheptanones were obtained in a trace amount or were not obtained at all. The enolate intermediates of this reaction were found to be able to get trapped with electrophiles to give 2,2,7-trisubstituted cycloheptanones in moderate to good yields. This method is very useful for the synthesis of 2,7-disubstituted cycloheptanones and 2,2,7-trisubstituted cycloheptanones from 2-substituted cyclohexanones in only two steps.

本文言語English
ページ(範囲)6769-6773
ページ数5
ジャーナルTetrahedron Letters
47
38
DOI
出版ステータスPublished - 2006 9 18
外部発表はい

ASJC Scopus subject areas

  • 生化学
  • 有機化学
  • 創薬

フィンガープリント

「One-carbon ring-expansion of 2-substituted cyclohexanones via lithium- and magnesium β-oxido carbenoid rearrangement: a new synthesis of 2,7-disubstituted and 2,2,7-trisubstituted cycloheptanones」の研究トピックを掘り下げます。これらがまとまってユニークなフィンガープリントを構成します。

引用スタイル