Palladium-catalyzed fluoride-free cross-coupling of intramolecularly activated alkenylsilanes and alkenylgermanes: Synthesis of tamoxifen as a synthetic application

Kenji Matsumoto, Mitsuru Shindo

研究成果: ジャーナルへの寄稿記事

24 引用 (Scopus)

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We have demonstrated that intramolecular hypercoordination of a carboxylic acid is a powerful activation strategy for the palladium-catalyzed cross-coupling reaction of trialkyl(vinyl)silanes and trialkyl(vinyl)germanes under fluoride-free conditions. Z-β-Trialkylsilyl- and Z-β- trialkylgermylacrylic acids, synthesized stereoselectively by olefination with ynolates, are highly stable and useful reagents for cross-coupling with a variety of aryl iodides to provide tetrasubstituted olefins possessing different carbon substituents in a stereocontrolled and diversity-oriented manner. An application to a stereoselective synthesis of (Z)-tamoxifen is also reported.

元の言語英語
ページ(範囲)642-650
ページ数9
ジャーナルAdvanced Synthesis and Catalysis
354
発行部数4
DOI
出版物ステータス出版済み - 3 1 2012

All Science Journal Classification (ASJC) codes

  • Catalysis
  • Organic Chemistry

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