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Updated: May 16, 2026

Versatile CO2 Transformations into Complex Products: A One-pot Two-step Strategy
Published on: November 9, 2019
One-pot sequential organocatalysis: highly stereoselective synthesis of trisubstituted cyclohexanols
Qipu Dai1, Hadi Arman, John Cong-Gui Zhao
1Department of Chemistry, University of Texas at San Antonio, One UTSA Circle, San Antonio, TX 78249, USA.
Abstract:
A highly diastereoselective (d.r. >99:1) and enantioselective (ee value up to 96%) synthesis of trisubstituted cyclohexanols was achieved by using a one-pot sequential organocatalysis that involved a quinidine thiourea-catalyzed tandem Henry-Michael reaction between nitromethane and 7-oxo-hept-5-en-1-als followed by a tetramethyl guanidine (TMG)-catalyzed tandem retro-Henry-Henry reaction on the reaction products of the tandem Henry-Michael reaction. Through a mechanistic study, it has also been demonstrated that similar results may also be achieved with this one-pot sequential organocatalysis by using the racemic Henry product as the substrate.
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