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

doi:10.1021/acs.orglett.7b01778

Paper

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

Published Jul 6, 2017 · DOI · J. Spencer, C. Jamieson, E. Talbot

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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.

Study Snapshot

This efficient one-pot procedure efficiently synthesizes complex cyclopropylboronic acid pinacol esters from synthetically tractable propargylic silyl ethers, offering a range of lead-like substituted cyclopropyl aryl products.

PopulationOlder adults (50-71 years)

Sample size24

MethodsObservational

OutcomesBody Mass Index projections

ResultsSocial networks mitigate obesity in older groups.

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

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