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Updated: Jul 15, 2026

Efficient Synthesis of All-Carbon Quaternary Centers via the Conjugate Addition of Functionalized Monoorganozinc Bromides
Published on: May 26, 2019
Highly diastereoselective synthesis of vicinal quaternary and tertiary stereocenters using the iodo-aldol cyclization
Frederic Douelle1, Amy S Capes, Michael F Greaney
1University of Edinburgh, School of Chemistry, Joseph Black Building, King's Buildings, Edinburgh, UK.
Abstract:
The intramolecular iodo-aldol cyclization of alpha-substituted enoate aldehydes and ketones is described. Using prochiral starting materials, the reaction produces hetero- and carbocycles containing quaternary centers adjacent to secondary or tertiary centers. The reactions occur in good yields and are highly selective for the trans-products, having the hydroxyl and iodomethyl groups on opposite faces of the ring system.
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