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Updated: Mar 24, 2026

Efficient Synthesis of All-Carbon Quaternary Centers via the Conjugate Addition of Functionalized Monoorganozinc Bromides
Published on: May 26, 2019
Concise Telescopic Total Synthesis of (±)-Mesembrine via Bi(OTf)3-Catalyzed Generation of a Quaternary Center
Rashmi Ranjan Khatua1, Faiz Ahmed Khan1
1Department of Chemistry, Indian Institute of Technology Hyderabad (IITH), Kandi, Sangareddy, Telangana 502285, India.
Abstract:
We describe a Bi(OTf)3-catalyzed annulation of methyl enol ethers with methyl vinyl ketone, providing rapid access to α-branched aldehyde quaternary carbon frameworks under mild conditions. The reaction tolerates diverse enol ethers, affording products in up to 95% yield. Application of this method enabled the total synthesis of (±)-mesembrine in 31% overall yield via a key α-quaternary aldehyde intermediate. Furthermore, a streamlined one-pot telescopic protocol enabled the direct synthesis of (±)-mesembrine in 30% yield without isolating intermediates.
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