Selective Synthesis of Ketones and Chiral Allylic Alcohols from the Addition of Arylboronic Acids to α,β-Unsaturated Aldehydes Mediated by a Transition Metal/Monophosphorus Ligand System

被引:4
作者
Miao, Rui [1 ]
Huang, Jinyong [1 ]
Xia, Yanping [1 ]
Wei, YiFei [1 ]
Luo, Renshi [1 ,2 ]
Ouyang, Lu [1 ]
机构
[1] Gannan Med Univ, Sch Pharm, Ganzhou 341000, Jiangxi, Peoples R China
[2] Shaoguan Univ, Coll Chem & Environm Engn, Shaoguan 512005, Guangdong, Peoples R China
基金
中国国家自然科学基金;
关键词
CATALYTIC ASYMMETRIC ARYLATION; ALPHA-ALKYLATION; ENANTIOSELECTIVE ADDITIONS; CONJUGATE REDUCTION; SECONDARY ALCOHOLS; ROOM-TEMPERATURE; HIGHLY EFFICIENT; ARYL; PALLADIUM; ISOMERIZATION;
D O I
10.1021/acs.joc.2c00703
中图分类号
O62 [有机化学];
学科分类号
070303 ; 081704 ;
摘要
Here, we demonstrated a transition metal-mediated/monophosphorus ligand system for the selective synthesis of ketones or chiral allylic alcohols in high yields/enantiomeric excess from the 1,2-addition of arylboronic acids to alpha,beta-unsaturated aldehydes. Notably, isomerization of the chiral allylic alcohols to ketones was suppressed by the Ru-catalyzed/monophosphorus ligand system. The asymmetric catalytic system provides an alternative and efficient method of preparing chiral allylic alcohols.
引用
收藏
页码:8576 / 8588
页数:13
相关论文
共 89 条
[1]   Scope and Mechanism of the Redox-Active 1,2-Benzoquinone Enabled Ruthenium-Catalyzed Deaminative α-Alkylation of Ketones with Amines [J].
Arachchige, Pandula T. Kirinde ;
Handunneththige, Suhashini ;
Talipov, Marat R. ;
Kalutharage, Nishantha ;
Yi, Chae S. .
ACS CATALYSIS, 2021, 11 (22) :13962-13972
[2]   Highly enantioselective hydrogenation of aryl vinyl ketones to allylic alcohols catalyzed by the tol-binap/dmapen ruthenium(II) complex [J].
Arai, Noriyoshi ;
Azuma, Keita ;
Nii, Noriyuki ;
Ohkuma, Takeshi .
ANGEWANDTE CHEMIE-INTERNATIONAL EDITION, 2008, 47 (39) :7457-7460
[3]   Synthesis and Structures of Arene Ruthenium (II)-NHC Complexes: Efficient Catalytic α-alkylation of ketones via Hydrogen Auto Transfer Reaction [J].
Balamurugan, Gunasekaran ;
Balaji, Sundarraman ;
Ramesh, Rengan ;
Bhuvanesh, Nattamai S. P. .
APPLIED ORGANOMETALLIC CHEMISTRY, 2019, 33 (01)
[4]   Reactions of Allylmagnesium Reagents with Carbonyl Compounds and Compounds with C=N Double Bonds: Their Diastereoselectivities Generally Cannot Be Analyzed Using the Felkin-Anh and Chelation-Control Models [J].
Bartolo, Nicole D. ;
Read, Jacquelyne A. ;
Valentin, Elizabeth M. ;
Woerpel, K. A. .
CHEMICAL REVIEWS, 2020, 120 (03) :1513-1619
[5]   Catalytic transfer reduction of conjugated alkenes and an imine using polymer-supported formates [J].
Basu, B ;
Bhuiyan, MH ;
Das, P ;
Hossain, I .
TETRAHEDRON LETTERS, 2003, 44 (50) :8931-8934
[6]   Palladium on carbon-catalyzed α-alkylation of ketones with alcohols as electrophiles: Scope and mechanism [J].
Bennedsen, Niklas R. ;
Mortensen, Rasmus L. ;
Kramer, Soren ;
Kegnaes, Soren .
JOURNAL OF CATALYSIS, 2019, 371 :153-160
[7]   Selective Catalytic Synthesis of α-Alkylated Ketones and β-Disubstituted Ketones via Acceptorless Dehydrogenative CrossCoupling of Alcohols [J].
Bhattacharyya, Dipanjan ;
Sarmah, Bikash Kumar ;
Nandi, Sekhar ;
Srivastava, Hemant Kumar ;
Das, Animesh .
ORGANIC LETTERS, 2021, 23 (03) :869-875
[8]  
Bolm C, 2000, ANGEW CHEM INT EDIT, V39, P3465, DOI 10.1002/1521-3773(20001002)39:19<3465::AID-ANIE3465>3.0.CO
[9]  
2-4
[10]  
Bolm C., 2001, ANGEW CHEM, V113, P1536