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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

Org Lett. 2017 Jul 21;19(14):3891-3894.

PMID: 28682080

Abstract:

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.

Chemicals Related in the Paper:

Catalog Number Product Name Structure CAS Number Price
AP126689018 Cyclopropylboronic acid pinacol ester Cyclopropylboronic acid pinacol ester 126689-01-8 Price
AP411235579 Cyclopropylboronic acid Cyclopropylboronic acid 411235-57-9 Price
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