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Updated: Jan 4, 2026

A Two-Step Protocol for Umpolung Functionalization of Ketones Via Enolonium Species
Published on: August 16, 2018
Enantioselective Synthesis of Cyclohexenol Derivatives from γ-Aryl-Substituted Enals via an Organocatalyzed
Debashis Majee1, Satish Jakkampudi1, Hadi D Arman1
1Department of Chemistry , University of Texas at San Antonio , One UTSA Circle , San Antonio , Texas 78249-0698 , United States.
Abstract:
A three-component reaction between γ-aryl-substituted α,β-unsaturated aldehydes and nitroalkenes was realized by using cinchona alkaloid-derived (thio)ureas and squaramides via the dienolate intermediates. This unprecedented 1,3- and 1,5-reactivity of dienolates of the γ-aryl-α,β-unsaturated aldehydes led to the formation of cyclohexenol derivatives with four contiguous stereogenic centers and a chiral substituent at C2 with good diastereoselectivities and high ee values. Such reactivities of the dienolates are totally different from those of the corresponding dienamine intermediates.
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