Dual Pathway for the Asymmetric Transfer Hydrogenation of α-Ketoimides to Chiral α-Hydroxy Imides or Chiral α-Hydroxy Esters

作者：Zhao, Qiankun; Zhao, Yuxi; Liao, Hang; Cheng, Tanyu; Liu, Guohua^*

来源：ChemCatChem, 2016, 8(2): 412-416.

DOI：10.1002/cctc.201500906

• asymmetric catalysis
• enantioselectivity
• hydrogenation
• ligand effects
• ruthenium

In an enantioselective reaction, we expect to obtain two types of chiral products through a controllable strategy in asymmetric catalysis. Herein, we develop Ru-catalysed asymmetric transfer hydrogenation of alpha-ketoimides to realise an enantioselective construction of chiral alpha-hydroxy imides or chiral a-hydroxy esters. The transformation of a-ketoimides catalysed by (S, S)-[RuCl(eta(6)-mesitylene)diamine] can afford various chiral alpha-hydroxy imides with high yields and enantioselectivities, whereas that catalysed by (S, S)-[RuCl(eta(6)-hexamethylbenzene)diamine] gives the desirable chiral alpha-hydroxy esters through a slight adjustment of the reaction conditions. The method described here is a controllable organic transformation with sodium formate as a hydrogen source under mild reaction conditions, and the benefit of this transformation is that various chiral a-hydroxy imides or alpha-hydroxy esters can be obtained selectively from alpha-ketoimides.

• 出版日期2016-1-20
• 单位上海师范大学