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

Spencer, Jonathan A. and Jamieson, Craig and Talbot, Eric P. A. (2017) One-pot, three-step synthesis of cyclopropylboronic acid pinacol esters from synthetically tractable propargylic silyl ethers. Organic Letters. ISSN 1523-7060 (https://doi.org/10.1021/acs.orglett.7b01778)

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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.

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• Item metadata

  Item type:	Article
  ID code:	61284
  Dates:	Date Event 6 July 2017 Published 6 July 2017 Published Online 12 June 2017 Accepted
  Subjects:	Science > Chemistry
  Department:	Faculty of Science > Pure and Applied Chemistry Strategic Research Themes > Health and Wellbeing
  Depositing user:	Pure Administrator
  Date deposited:	18 Jul 2017 15:53
  Last modified:	16 Apr 2024 00:21
  Related URLs:	Journal or Publication
  URI:	https://strathprints.strath.ac.uk/id/eprint/61284