One-Pot Sequential Organocatalysis: Highly Stereoselective Synthesis of Trisubstituted Cyclohexanols

Authors

  • Dr. Qipu Dai,

    1. Department of Chemistry, University of Texas at San Antonio, One UTSA Circle, San Antonio, TX 78249 (USA), Fax: (+1) 210-458-7428
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  • Dr. Hadi Arman,

    1. Department of Chemistry, University of Texas at San Antonio, One UTSA Circle, San Antonio, TX 78249 (USA), Fax: (+1) 210-458-7428
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  • Prof. Dr. John Cong-Gui Zhao

    Corresponding author
    1. Department of Chemistry, University of Texas at San Antonio, One UTSA Circle, San Antonio, TX 78249 (USA), Fax: (+1) 210-458-7428
    • Department of Chemistry, University of Texas at San Antonio, One UTSA Circle, San Antonio, TX 78249 (USA), Fax: (+1) 210-458-7428
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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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