Organic Letters
Organic Letters
5 years ago

One-Pot, Three-Step Synthesis of Cyclopropylboronic Acid Pinacol Esters from Synthetically Tractable Propargylic Silyl Ethers

One-Pot, Three-Step Synthesis of Cyclopropylboronic Acid Pinacol Esters from Synthetically Tractable Propargylic Silyl Ethers
Craig Jamieson, Jonathan A. Spencer, Eric P. A. Talbot
Simple propargylic silyl ethers can be converted to complex cyclopropylboronic acid pinacol esters in an efficient one-pot 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.

Publisher URL: http://dx.doi.org/10.1021/acs.orglett.7b01778

DOI: 10.1021/acs.orglett.7b01778

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