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Ru–Prolinamide‐Catalyzed Asymmetric Transfer Hydrogenation of Racemic β‐Heterosubstituted Cycloalkanones Driven by Dynamic Kinetic Resolution
Asian Journal of Organic Chemistry ( IF 2.7 ) Pub Date : 2018-01-15 , DOI: 10.1002/ajoc.201700688
Vijyesh K. Vyas 1 , Bhalchandra M. Bhanage 1
Affiliation  

A ruthenium–prolinamide catalytic system has been applied for the first time in dynamic kinetic resolution/asymmetric transfer hydrogenation reactions (DKR/ATH) in aqueous medium to synthesize cis‐β‐heterosubstituted cycloalkanols with two contiguous chiral centers. The effect of various prolinamide ligands in DKR/ATH has been studied on different racemic‐β‐heterosubstituted cycloalkanones. A prolinamide ligand with a bulky substituent at an ortho position proves to be more effective than the previously reported ruthenium–TsDPEN catalytic system in aqueous medium, producing up to 99.1 % enantioselectivity and 99:1 diastereoselectivity.

中文翻译:

动态动力学拆分驱动Ru-脯氨酰胺催化外消旋β-杂取代环烷酮的不对称转移加氢

钌-脯氨酰胺催化体系首次在水介质中用于动态动力学拆分/不对称转移氢化反应(DKR / ATH)中,以合成具有两个连续手性中心的顺式-β-杂取代环烷醇。研究了DKR / ATH中各种脯氨酰胺配体对不同外消旋-β-杂取代的环烷酮的影响。在水性介质中,在邻位具有较大取代基的脯氨酰胺配体被证明比先前报道的钌-TsDPEN催化体系更有效,对映选择性高达99.1%,非对映选择性高达99:1。
更新日期:2018-01-15
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