RuPHOX-Ru catalyzed asymmetric Guerbet reaction of secondary alcohols with primary alcohols

被引:3
作者
He, Jingli [1 ]
Li, Ruhui [1 ]
Kou, Xuezhen [1 ]
Fu, Daxu [2 ]
Liu, Delong [1 ]
Zhang, Wanbin [1 ,3 ]
机构
[1] Shanghai Jiao Tong Univ, Sch Pharm, Shanghai Key Lab Mol Engn Chiral Drugs, 800 Dongchuan Rd, Shanghai 200240, Peoples R China
[2] Shanghai Inst Biomed & Pharmaceut Technol, 779 Laohumin Rd, Shanghai 200237, Peoples R China
[3] Shanghai Jiao Tong Univ, Frontier Sci Ctr Transformat Mol, Sch Chem & Chem Engn, 800 Dongchuan Rd, Shanghai 200240, Peoples R China
基金
中国国家自然科学基金;
关键词
RuPHOX-Ru; Asymmetric Guerbet reaction; Long-chain chiral alcohol; CHIRAL-GAMMA-LACTONES; TRANSFER HYDROGENATION; AMINO KETONES; IRIDIUM CATALYSTS; BETA-ALKYLATION; METHYL KETONES; METAL; LIGANDS; COMPLEXES; CYCLOALKANES;
D O I
10.1016/j.tet.2023.133543
中图分类号
O62 [有机化学];
学科分类号
070303 ; 081704 ;
摘要
An efficient RuPHOX-Ru catalyzed asymmetric Guerbet reaction of secondary alcohols with a broad scope of primary alcohols has been developed, affording long-chain chiral alcohols in high yields with excellent enantioselectivities (up to 99% yield and 96% ee). In particular, alkyl primary alcohols could also react to give the desired products with good results. The protocol could be performed on a gram-scale, providing an alternative pathway with minimal environmental impact and high atom-economy for the preparation of chiral alcohol products. & COPY; 2023 Elsevier Ltd. All rights reserved.
引用
收藏
页数:9
相关论文
共 50 条
[41]   Catalytic -Alkylation/Reduction of Ketones with Primary Alcohols To Furnish Secondary Alcohols [J].
Lundberg, Helena ;
Adolfsson, Hans .
SYNTHESIS-STUTTGART, 2016, 48 (05) :644-652
[42]   Dehydrogenative Cross-Coupling of Primary and Secondary Alcohols [J].
Musa, Sanaa ;
Ackermann, Lutz ;
Gelman, Dmitri .
ADVANCED SYNTHESIS & CATALYSIS, 2013, 355 (14-15) :3077-3080
[43]   Ruthenium-Catalyzed Self-Coupling of Secondary Alcohols [J].
Kumar, Nitin ;
Sankar, Raman Vijaya ;
Gunanathan, Chidambaram .
JOURNAL OF ORGANIC CHEMISTRY, 2023, 88 (24) :17155-17163
[44]   Transformation of Alkynes into Chiral Alcohols via TfOH-Catalyzed Hydration and Ru-Catalyzed Tandem Asymmetric Hydrogenation [J].
Liu, Sensheng ;
Liu, Huan ;
Zhou, Haifeng ;
Liu, Qixing ;
Lv, Jinliang .
ORGANIC LETTERS, 2018, 20 (04) :1110-1113
[45]   Ru-NHC Catalyzed Domino Reaction of Carbonyl Compounds and Alcohols: A Short Synthesis of Donaxaridine [J].
Bisht, Girish Singh ;
Chaudhari, Moreshwar Bhagwan ;
Gupte, Vruta Sunil ;
Gnanaprakasam, Boopathy .
ACS OMEGA, 2017, 2 (11) :8234-8252
[46]   Tandem α-Alkylation/Asymmetric Transfer Hydrogenation of Acetophenones with Primary Alcohols [J].
Kovalenko, Oleksandr O. ;
Lundberg, Helena ;
Huebner, Dennis ;
Adolfsson, Hans .
EUROPEAN JOURNAL OF ORGANIC CHEMISTRY, 2014, 2014 (30) :6639-6642
[47]   Redox-driven deracemization of secondary alcohols by sequential ether/O2 -mediated oxidation and Ru-catalyzed asymmetric reduction [J].
Yang, Bing ;
Cui, Peng ;
Chen, Yongsheng ;
Liu, Qixing ;
Zhou, Haifeng .
TETRAHEDRON LETTERS, 2020, 61 (46)
[48]   Ru(II)-Triphos Catalyzed Amination of Alcohols with Ammonia via Ionic Species [J].
Derrah, Eric J. ;
Hanauer, Matthias ;
Plessow, Philipp N. ;
Schelwies, Mathias ;
da Silva, Marion K. ;
Schaub, Thomas .
ORGANOMETALLICS, 2015, 34 (10) :1872-1881
[49]   Bimetallic Pt-Sn/γ-Al2O3 catalyzed β-alkylation of secondary alcohols with primary alcohols under solvent-free conditions [J].
Wu, Kaikai ;
He, Wei ;
Sun, Chenglin ;
Yu, Zhengkun .
TETRAHEDRON LETTERS, 2016, 57 (36) :4017-4020
[50]   Ruthenium-Catalyzed Self-Coupling of Primary and Secondary Alcohols with the Liberation of Dihydrogen [J].
Makarov, Ilya S. ;
Madsen, Robert .
JOURNAL OF ORGANIC CHEMISTRY, 2013, 78 (13) :6593-6598