Rh(I)-catalyzed regio- and enantioselective allylic alkylation of Meldrum's acid

被引:16
作者
Liu, Min [1 ]
Zhao, Haiying [1 ]
Li, Changkun [2 ]
机构
[1] Inner Mongolia Univ, Coll Chem & Chem Engn, Inner Mongolia Key Lab Fine Organ Synth, Hohhot 010021, Peoples R China
[2] Shanghai Jiao Tong Univ, Sch Chem & Chem Engn, Shanghai Key Lab Mol Engn Chiral Drugs, Shanghai 200240, Peoples R China
基金
中国国家自然科学基金;
关键词
Rhodium; Bisoxazolinephosphine; Allylic substitution; Meldrum's acid; Asymmetric catalysis;
D O I
10.1016/j.cclet.2020.04.009
中图分类号
O6 [化学];
学科分类号
0703 ;
摘要
A Rh(I)-catalyzed highly regio- and enantioselective allylic alkylation of Meldrum acid with racemic allylic substrates bearing alkyl groups has been developed. The applying of chiral bisoxazopinephosphine ligand is essential for the high yields and selectivities. This method provides a rapid access to various chiral beta-alkyl-gamma,delta-unsaturated carboxylic acids and their derivatives. (C) 2020 Chinese Chemical Society and Institute of Materia Medica, Chinese Academy of Medical Sciences. Published by Elsevier B.V. All rights reserved.
引用
收藏
页码:385 / 388
页数:4
相关论文
共 34 条
[1]   Enantioselective Intermolecular Pd-Catalyzed Hydroalkylation of Acyclic 1,3-Dienes with Activated Pronucleophiles [J].
Adamson, Nathan J. ;
Wilbur, Katherine C. E. ;
Malcolmson, Steven J. .
JOURNAL OF THE AMERICAN CHEMICAL SOCIETY, 2018, 140 (08) :2761-2764
[2]   Substituted aryl malonamates as new serine β-lactamase substrates: Structure-activity studies [J].
Adediran, S. A. ;
Cabaret, D. ;
Lohier, J. -F. ;
Wakselman, M. ;
Pratt, R. F. .
BIOORGANIC & MEDICINAL CHEMISTRY, 2010, 18 (01) :282-291
[3]   Convenient preparation and use of a new analytical construct for the analysis and development of solid-phase chemistries [J].
Andrews, SP ;
Ladlow, M .
JOURNAL OF ORGANIC CHEMISTRY, 2003, 68 (14) :5525-5533
[4]   Iridium-Catalyzed Asymmetric Allylic Substitution Reactions [J].
Cheng, Qiang ;
Tu, Hang-Fei ;
Zheng, Chao ;
Qu, Jian-Ping ;
Helmchen, Guenter ;
You, Shu-Li .
CHEMICAL REVIEWS, 2019, 119 (03) :1855-1969
[5]   Meldrum's Acids and 5-Alkylidene Meldrum's Acids in Catalytic Carbon-Carbon Bond-Forming Processes [J].
Dumas, Aaron M. ;
Fillion, Eric .
ACCOUNTS OF CHEMICAL RESEARCH, 2010, 43 (03) :440-454
[6]   Practical Pd/C-mediated allylic substitution in water [J].
Felpin, FX ;
Landais, Y .
JOURNAL OF ORGANIC CHEMISTRY, 2005, 70 (16) :6441-6446
[7]   Lewis Base-Promoted Hydrosilylation of Cyclic Malonates: Synthesis of β-Substituted Aldehydes and γ-Substituted Amines [J].
Frost, Christopher G. ;
Hartley, Benjamin C. .
JOURNAL OF ORGANIC CHEMISTRY, 2009, 74 (09) :3599-3602
[8]   Cobalt-Catalyzed Regio- and Enantioselective Allylic Amination [J].
Ghorai, Samir ;
Chirke, Sahadev Shrihari ;
Xu, Wen-Bin ;
Chen, Jia-Feng ;
Li, Changkun .
JOURNAL OF THE AMERICAN CHEMICAL SOCIETY, 2019, 141 (29) :11430-11434
[9]  
Kazmaier U, 2012, TOP ORGANOMETAL CHEM, V38, P1, DOI 10.1007/978-3-642-22749-3
[10]   An Adverse Effect of Higher Catalyst Loading and Longer Reaction Time on Enantioselectivity in an Organocatalytic Multicomponent Reaction [J].
Khopade, Tushar M. ;
Mete, Trimbak B. ;
Arora, Jyotsna S. ;
Bhat, Ramakrishna G. .
CHEMISTRY-A EUROPEAN JOURNAL, 2018, 24 (23) :6036-6040