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Updated: Jun 7, 2026

Efficient Synthesis of All-Carbon Quaternary Centers via the Conjugate Addition of Functionalized Monoorganozinc Bromides
Published on: May 26, 2019
Practical access to highly enantioenriched quaternary carbon Michael adducts using simple organocatalysts
Thomas C Nugent1, Mohammad Shoaib, Amna Shoaib
1Department of Chemistry, School of Engineering and Science, Jacobs University Bremen, Campus Ring 1, 28759 Bremen, Germany. t.nugent@jacobs-university.de
Abstract:
A three component catalyst system entailing an amino acid (O(t)Bu-L-threonine), a hydrogen bond donor (sulfamide), and an amine base (DMAP) allows α-branched aldehyde addition to nitroalkenes in good to high yield and excellent ee. Importantly, the lowest reported catalyst loading (5.0 mol%) and aldehyde stoichiometry (1.2-2.0 equiv) is demonstrated and in most instances the best current product profile is observed.
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