Synthesis of Chiral Aromatic Alcohols: Use of New C2-Symmetric RhIIICp?, RuII(cymene), or RuII(benzene) Complexes Containing Chiral Diaminocyclohexane Ligand as Asymmetric Transfer Hydrogenation Catalyst |
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| Authors: | Rubén Montalvo-González Daniel Chávez Gerardo Aguirre Miguel Parra-Hake |
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| Institution: | 1. Graduate and Research Center , Tijuana Technological Institute , Tijuana, México;2. Academic Unit of Chemistry, Biology and Pharmaceutical Sciences , Nayarit Autonomous University , Tepic, Nayarit, México;3. Graduate and Research Center , Tijuana Technological Institute , Tijuana, México |
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| Abstract: | Abstract Twelve chiral secondary alcohols were synthesized by asymmetric transfer hydrogenation (ATH) using C2-symmetric bis(sulfonamide) ligand (2) derived from (1R,2R)-cyclohexane-1,2-diamine and complexed with RhCl2Cp?]2, RuCl2(cymene)]2, or RuCl2(benzene)]2 and then used in situ in the reduction of prochiral ketones. The alcohols were obtained in 85–99% yield and 90–99% enantioselectivity with isopropanol as the hydrogen source. Two-fold rate enhancement and better yields were achieved (88–99%) with 80–99% enantioselectivity using the complex RhCl2Cp?]2 and aqueous sodium formate as the hydrogen source. |
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| Keywords: | Bis(sulfonamide) ligands chiral secondary alcohols RuII(arene) RhIIICp? |
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