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Updated: Jun 15, 2026

Efficient Synthesis of All-Carbon Quaternary Centers via the Conjugate Addition of Functionalized Monoorganozinc Bromides
Published on: May 26, 2019
Structural elaboration of the surprising ortho-zincation of benzyl methyl ether
Liam Balloch1, Alan R Kennedy, Jan Klett
1WestCHEM, Department of Pure and Applied Chemistry, University of Strathclyde, Glasgow, UK G1 1XL.
Abstract:
Breaking with convention, the reaction of the sodium zincate, [(TMEDA)Na(mu-TMP)(mu-(t)Bu)Zn((t)Bu)] with benzyl methyl ether (PhCH(2)OMe) produces exclusively an ortho-zincated intermediate [(TMEDA)Na(mu-TMP)(mu-C(6)H(4)CH(2)OMe)Zn((t)Bu)] instead of the expected "thermodynamic" alpha-metallated product.
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