Details

Autor(en) / Beteiligte

• Lu, Bin
• Wu, Xiaoyu
• Li, Chengyang
• Ding, Guangni
• Li, Wanfang
• Xie, Xiaomin
• Zhang, Zhaoguo

Titel

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

Ist Teil von

• Journal of organic chemistry, 2019-03, Vol.84 (6), p.3201-3213

Ort / Verlag

United States: American Chemical Society

Erscheinungsjahr

2019

Link zum Volltext

Quelle

Alma/SFX Local Collection

Beschreibungen/Notizen

• 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.