Highly Diastereo- and Enantioselective Access to syn-α-Amido β-Hydroxy Esters via Ruthenium-Catalyzed Dynamic Kinetic Resolution-Asymmetric Hydrogenation

被引：13

作者：

Lu, Bin ^{[1
]}

Wu, Xiaoyu ^{[1
]}

Li, Chengyang ^{[1
]}

Ding, Guangni ^{[1
]}

Li, Wanfang ^{[1
]}

Xie, Xiaomin ^{[1
]}

Zhang, Zhaoguo ^{[1
,2
]}

机构：

[1] Shanghai Jiao Tong Univ, Sch Chem & Chem Engn, Shanghai Key Lab Mol Engn Chiral Drugs, 800 Dongchuan Rd, Shanghai 200240, Peoples R China

[2] Chinese Acad Sci, Shanghai Inst Organ Chem, 345 Lingling Rd, Shanghai 200032, Peoples R China

来源：

JOURNAL OF ORGANIC CHEMISTRY | 2019年 / 84卷 / 06期

基金：

中国国家自然科学基金;

关键词：

ORGANOCATALYTIC ANTI-MANNICH; AMINO-ACIDS; EFFICIENT SYNTHESIS; STEREOSELECTIVE HYDROGENATION; KETO-ESTERS; D-THREONINE; ROUTE; COMPLEXES; DERIVATIVES; PRECURSORS;

D O I：

10.1021/acs.joc.8b03106

中图分类号：

O62 [有机化学];

学科分类号：

070303 ; 081704 ;

摘要：

Dynamic kinetic resolution (DKR) of racemic aryl alpha-amino beta-ketoesters via Ru-diphosphine-catalyzed asymmetric hydrogenation was realized at 70 degrees C under 50 atm of hydrogen, affording syn alpha-amido beta-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.

引用

页码：3201 / 3213

页数：13

共 71 条

[1] Advances in Stereoconvergent Catalysis from 2005 to 2015: Transition-Metal-Mediated Stereoablative Reactions, Dynamic Kinetic Resolutions, and Dynamic Kinetic Asymmetric Transformations [J].