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Updated: Mar 28, 2026

Efficient Synthesis of All-Carbon Quaternary Centers via the Conjugate Addition of Functionalized Monoorganozinc Bromides
Published on: May 26, 2019
An expedient synthesis of functionalized 1,4-diketone-derived compounds via silyloxyallyl cation intermediates
Jacob R Stepherson1, Frank R Fronczek1, Rendy Kartika1
1Department of Chemistry, 232 Choppin Hall, Louisiana State University, Baton Rouge, LA 70803, USA. rkartika@lsu.edu.
Abstract:
Herein we describe a new method, enabling the synthesis of highly functionalized 1,4-diketones that are readily differentiated as monosilylenol ethers under Brønsted acid catalysis. This synthetically useful chemistry exploited an intermediacy of unsymmetrical silyloxyallyl cations, which were directly captured by silyl enolates to create the targeted α,α carbon-carbon linkages in a regioselective manner. Our reaction conditions proved to be mild, rendering the silylenol ether functionalities intact.
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