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

Tools

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)

[thumbnail of Spencer-etal-OL-2017-One-pot-three-step-synthesis-of-cyclopropylboronic-acid]
Preview
 Text. Filename: Spencer_etal_OL_2017_One_pot_three_step_synthesis_of_cyclopropylboronic_acid.pdf
Accepted Author Manuscript
Download (970kB)| Preview

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.

ORCID iDs

Spencer, Jonathan A. ORCID logoORCID: https://orcid.org/0000-0001-9693-9538, Jamieson, Craig ORCID logoORCID: https://orcid.org/0000-0002-6567-8272 and Talbot, Eric P. A.;
CORE (COnnecting REpositories)