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Updated: Jul 5, 2026

Efficient Synthesis of All-Carbon Quaternary Centers via the Conjugate Addition of Functionalized Monoorganozinc Bromides
Published on: May 26, 2019
Lewis acid-catalyzed conjugate additions of silyloxyallenes: a selective solution to the intermolecular
Troy E Reynolds1, Michael S Binkley, Karl A Scheidt
1Department of Chemistry, Northwestern University, Evanston, IL 60208, USA.
Abstract:
Silyloxyallenes serve as highly useful alpha-acylvinyl anion equivalents. These latent allenolates undergo conjugate additions to alkylidene malonates in the presence of 10 mol % Sc(OTf) 3. The reaction delivers intermolecular Rauhut-Currier products in excellent yields and regioselectivities for a wide scope of substrates. Notably, the formal cross-coupling of two different alpha,beta-unsaturated carbonyl compounds (a cross Rauhut-Currier reaction) is achieved. Preliminary investigations have demonstrated good levels of enantioselectivity for the addition of a racemic silyloxyallene with a chiral Lewis acid.
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