Chiral Surfactant-Type Catalyst for Asymmetric Reduction of Aliphatic Ketones in Water

被引：125

作者：

Li, Jiahong ^{[2
,4
]}

Tang, Yuanfu ^{[2
,4
]}

Wang, Qiwei ^{[2
]}

Li, Xuefeng ^{[3
]}

Cun, Linfeng ^{[2
]}

Zhang, Xiaomei ^{[2
]}

Zhu, Jin ^{[2
]}

Li, Liangchun ^{[1
]}

Deng, Jingen ^{[1
]}

机构：

[1] Sichuan Univ, Key Lab Drug Targeting, Educ Minist, W China Sch Pharm, Chengdu 610041, Peoples R China

[2] Chinese Acad Sci, Chengdu Inst Organ Chem, Chengdu 610041, Peoples R China

[3] SW Univ Nationalities, Coll Chem & Environm Protect Engn, Chengdu 610041, Peoples R China

[4] Chinese Acad Sci, Grad Univ, Beijing 100049, Peoples R China

来源：

JOURNAL OF THE AMERICAN CHEMICAL SOCIETY | 2012年 / 134卷 / 45期

基金：

中国国家自然科学基金;

关键词：

ENANTIOSELECTIVE TRANSFER HYDROGENATION; ALDOL REACTIONS; COMPLEXES; ALKYL; HYDROSILYLATION; DERIVATIVES; MICELLES; ALCOHOLS;

D O I：

10.1021/ja308357y

中图分类号：

O6 [化学];

学科分类号：

0703 ;

摘要：

A novel chiral surfactant-type catalyst is developed. Micelles formed in water by association of the catalysts themselves, and this was confirmed by TEM analyses. Asymmetric transfer hydrogenation of aliphatic ketones catalyzed by the chiral metallomicellar catalyst gave good to excellent conversions and remarkable stereoselectivities (up to 95% ee). Synergistic effects between the metal catalyzed center and the hydrophobic microenvironment of the core in the metallomicelle led to high enantioselectivities.

引用

页码：18522 / 18525

页数：4

共 45 条

[21] Asymmetric Transfer Hydrogenation of Prochiral Ketones in Aqueous Media with Chiral Water-Soluble and Heterogenized Bifunctional Catalysts of the RhCp*-Type Ligand
Barron-Jaime, Angelica
Narvaez-Garayzar, Oscar F.
Ganzalez, Jorge
Ibarra-Galvan, Valentin
Aguirre, Gerardo
Parra-Hake, Miguel
Chavez, Daniel
Somanathan, Ratnasamy
CHIRALITY, 2011, 23 (02) : 178 - 184
[22] Asymmetric reduction of α-hydroxy aromatic ketones to chiral aryl vicinal diols using carrot enzymes system
Liu, Xiang
Wang, Yi
Gao, Hai Yan
Xu, Jian He
CHINESE CHEMICAL LETTERS, 2012, 23 (06) : 635 - 638
[23] A novel C3-symmetric prolinol-squaramide catalyst for the asymmetric reduction of ketones by borane
Wu, Xiang-Fei
Min, Chang
Nyamzundui, Enkhtsetseg
Zhou, Hai-Bing
Dong, Chune
TETRAHEDRON-ASYMMETRY, 2011, 22 (16-17) : 1640 - 1643
[24] Polymer-Supported Chiral Heterogeneous Copper Catalyst for Asymmetric Conjugate Addition of Ketones and Imines under Batch and Flow
Wang, Junwen
Li, Jun
Wang, Yan
He, Sisi
You, Hengzhi
Chen, Fen -Er
ACS CATALYSIS, 2022, 12 (15) : 9629 - 9637
[25] The synthesis of chiral N-heterocyclic carbene-borane and -diorganoborane complexes and their use in the asymmetric reduction of ketones
Lindsay, David M.
McArthur, David
CHEMICAL COMMUNICATIONS, 2010, 46 (14) : 2474 - 2476
[26] Iron-Catalyzed Highly Enantioselective Reduction of Aromatic Ketones with Chiral P2N4-Type Macrocycles
Yu, Shenluan
Shen, Weiyi
Li, Yanyun
Dong, Zhenrong
Xu, Yaqing
Li, Qi
Zhang, Juanni
Gao, Jingxing
ADVANCED SYNTHESIS & CATALYSIS, 2012, 354 (05) : 818 - 822
[27] Designing Chiral Quaternary Ammonium Polymers: Novel Type of Polymeric Catalyst for Asymmetric Alkylation Reaction
Itsuno, Shinichi
Paul, Devproshad K.
Ishimoto, Mikiya
Haraguchi, Naoki
CHEMISTRY LETTERS, 2010, 39 (02) : 86 - 87
[28] Asymmetric Transfer Hydrogenation of Imines and Ketones Using Chiral RuIICl(η6-p-cymene)[(S,S)-N-TsDPEN] as a Catalyst: A Computational Study
Vaclavik, Jiri
Kuzma, Marek
Prech, Jan
Kacer, Petr
ORGANOMETALLICS, 2011, 30 (18) : 4822 - 4829
[29] (η6-Arene)RuII/Chiral SN Ligand: A Novel Bifunctional Catalyst System for Asymmetric Transfer Hydrogenation of Aromatic Ketones
Ito, Masato
Shibata, Yuji
Watanabe, Akira
Ikariya, Takao
SYNLETT, 2009, (10) : 1621 - 1626
[30] Highly asymmetric aldol reaction of isatins and ketones catalyzed by chiral bifunctional primary-amine organocatalyst on water
Lv, Xiao-Xiong
Liu, Ning
Chen, Fei
Zhang, Hao
Du, Zhi-Hong
Wang, Pei
Yuan, Meng
Da, Chao Shan
ORGANIC & BIOMOLECULAR CHEMISTRY, 2023, 21 (43) : 8695 - 8701

← 1 2 3 4 5 →