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Updated: Apr 5, 2026

A Two-Step Protocol for Umpolung Functionalization of Ketones Via Enolonium Species
Published on: August 16, 2018
Iterative Coupling of Two Different Enones by Nitromethane Using Bifunctional Thiourea Organocatalysts.
Szilárd Varga1, Gergely Jakab1, Antal Csámpai2
1Institute of Organic Chemistry, Research Centre for Natural Sciences, HAS , P.O. Box 286, Budapest, H-1519, Hungary.
Abstract:
An organocatalytic iterative assembly line has been developed in which nitromethane was sequentially coupled with two different enones using a combination of pseudoenantiomeric cinchona-based thiourea catalysts. Application of unsaturated aldehydes and ketones in the second step of the iterative sequence allows the construction of cyclic syn-ketols and acyclic compounds with multiple contiguous stereocenters. The combination of the multifunctional substrates and ambident electrophiles rendered some organocatalytic transformations possible that have not yet been realized in bifunctional noncovalent organocatalysis.
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