One-pot, three-step synthesis of cyclopropylboronic acid pinacol esters from synthetically tractable propargylic silyl ethers

Jonathan A. Spencer, Craig Jamieson, Eric P. A. Talbot

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Abstract

Simple propargylic silyl ethers can be converted to complex cyclopropylboronic acid pinacol esters in an efficient onepot procedure. Terminal acetylenes undergo a Schwartz’s reagent catalyzed hydroboration; subsequent addition of further Schwartz’s reagent and Lewis acid-mediated activation of neighboring silyl ether allows cyclization to access a range of cyclopropylboronic acid pinacol esters. The scope includes aromatic, aliphatic, quaternary, and spiro substituted cyclopropyl rings, which can be transformed via Suzuki coupling into a range of lead-like substituted cyclopropyl aryl products.
Original languageEnglish
Number of pages4
JournalOrganic Letters
Early online date6 Jul 2017
DOIs
Publication statusE-pub ahead of print - 6 Jul 2017

Keywords

  • Suzuki coupling
  • cyclopropyl aryl
  • propargylic silyl ether

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