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

Kenji Matsumoto, Mitsuru Shindo

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23 Citations (Scopus)

Abstract

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.

Original languageEnglish
Pages (from-to)642-650
Number of pages9
JournalAdvanced Synthesis and Catalysis
Volume354
Issue number4
DOIs
Publication statusPublished - Mar 1 2012

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All Science Journal Classification (ASJC) codes

  • Catalysis
  • Organic Chemistry

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