通过钌催化的动态动力学拆分-不对称氢化反应，高非对映选择性和对映选择性地获得 syn-α-酰胺 β-羟基酯。
Highly Diastereo- and Enantioselective Access to syn-α-Amido β-Hydroxy Esters via Ruthenium-Catalyzed Dynamic Kinetic Resolution-Asymmetric Hydrogenation.
机构信息
Shanghai Key Laboratory for Molecular Engineering of Chiral Drugs, School of Chemistry and Chemical Engineering , Shanghai Jiao Tong University , 800 Dongchuan Road , Shanghai 200240 , China.
Shanghai Institute of Organic Chemistry , Chinese Academy of Sciences , 345 Lingling Road , Shanghai 200032 , China.
出版信息
J Org Chem. 2019 Mar 15;84(6):3201-3213. doi: 10.1021/acs.joc.8b03106. Epub 2019 Mar 1.
Dynamic kinetic resolution (DKR) of racemic aryl α-amino β-ketoesters via Ru-diphosphine-catalyzed asymmetric hydrogenation was realized at 70 °C under 50 atm of hydrogen, affording syn α-amido β-hydroxy esters in high yields (up to 96%) with high reactivity (TON up to 940) and diastereo- and enantioselectivities (up to 99:1 dr, 98% ee). These hydrogenation products provide valuable chiral synthons in many natural products and pharmaceuticals. Gram-scale DKR asymmetric hydrogenation (DKR-AH) was also performed with retained reactivity and stereoselectivity, revealing the synthetic utility of this method.
通过 Ru-二膦配体催化的不对称氢化反应，可以在 70°C、50 个大气压的氢气条件下实现外消旋芳基α-氨基β-酮酯的动态动力学拆分，以高收率（高达 96%）、高反应性（TON 高达 940）和非对映选择性和对映选择性（高达 99:1 dr，98%ee）得到顺式α-酰胺基β-羟基酯。这些氢化产物为许多天然产物和药物中的有价值的手性合成子提供了条件。克级规模的 DKR 不对称氢化（DKR-AH）也具有保留的反应性和立体选择性，这揭示了该方法的合成实用性。
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