title: Chiral surfactant-type catalyst: enantioselective reduction of long-chain aliphatic ketoesters in water.
abstract: A series of amphiphilic ligands were designed and synthesized. The rhodium complexes with the ligands were applied to the asymmetric transfer hydrogenation of broad range of long-chained aliphatic ketoesters in neat water. Quantitative conversion and excellent enantioselectivity (up to 99% ee) was observed for α-, β-, γ-, δ- and ε-ketoesters as well as for α- and β-acyloxyketone using chiral surfactant-type catalyst 2. The CH/π interaction and the strong hydrophobic interaction of long aliphatic chains between the catalyst and the substrate in the metallomicelle core played a key role in the catalytic transition state. Synergistic effects between the metal-catalyzed site and the hydrophobic microenvironment of the core in the micelle contributed to high stereoselectivity.
authors.affiliation: †Chengdu Institute of Organic Chemistry, Chinese Academy of Sciences, Chengdu 610041, China.|§Graduate University of Chinese Academy of Sciences, Beijing 100049, China.
authors.forename: Zechao
authors.initials: Z
authors.lastname: Lin
authors.affiliation: †Chengdu Institute of Organic Chemistry, Chinese Academy of Sciences, Chengdu 610041, China.|§Graduate University of Chinese Academy of Sciences, Beijing 100049, China.
authors.forename: Jiahong
authors.initials: J
authors.lastname: Li
authors.affiliation: †Chengdu Institute of Organic Chemistry, Chinese Academy of Sciences, Chengdu 610041, China.
authors.forename: Qingfei
authors.initials: Q
authors.lastname: Huang
authors.affiliation: †Chengdu Institute of Organic Chemistry, Chinese Academy of Sciences, Chengdu 610041, China.
authors.forename: Qiuya
authors.initials: Q
authors.lastname: Huang
authors.affiliation: †Chengdu Institute of Organic Chemistry, Chinese Academy of Sciences, Chengdu 610041, China.
authors.forename: Qiwei
authors.initials: Q
authors.lastname: Wang
authors.affiliation: #Laboratory of Anesthesia and Critical Care Medicine, Translational Neuroscience Center, West China Hospital, Sichuan University, Chengdu 610041, China.
authors.forename: Lei
authors.initials: L
authors.lastname: Tang
authors.affiliation: #Laboratory of Anesthesia and Critical Care Medicine, Translational Neuroscience Center, West China Hospital, Sichuan University, Chengdu 610041, China.
authors.forename: Deying
authors.initials: D
authors.lastname: Gong
authors.affiliation: #Laboratory of Anesthesia and Critical Care Medicine, Translational Neuroscience Center, West China Hospital, Sichuan University, Chengdu 610041, China.
authors.forename: Jun
authors.initials: J
authors.lastname: Yang
authors.affiliation: †Chengdu Institute of Organic Chemistry, Chinese Academy of Sciences, Chengdu 610041, China.
authors.forename: Jin
authors.initials: J
authors.lastname: Zhu
authors.affiliation: †Chengdu Institute of Organic Chemistry, Chinese Academy of Sciences, Chengdu 610041, China.|‡Key Laboratory of Drug-Targeting of Education Ministry, West China School of Pharmacy, Sichuan University, Chengdu 610041, China.
authors.forename: Jingen
authors.initials: J
authors.lastname: Deng
mesh_terms: D002384:Catalysis; D004952:Esters / Q000737:chemistry*; D006863:Hydrogen-Ion Concentration; D015394:Molecular Structure; D010084:Oxidation-Reduction; D013237:Stereoisomerism; D013501:Surface-Active Agents / Q000737:chemistry*; D014867:Water / Q000737:chemistry*
chemical_list: D004952:Esters; D013501:Surface-Active Agents; D014867:Water