Synthesis of Tetrahydroisoindolinones via a Metal-Free Dehydrogenative Diels-Alder Reaction

被引:13
作者
Xu, Wen-Lei [1 ]
Tang, Lei [1 ]
Ge, Chen-Yu [1 ]
Chen, Jie [1 ]
Zhou, Ling [1 ]
机构
[1] Northwest Univ, Natl Demonstrat Ctr Expt Chem Educ, Coll Chem & Mat Sci, Key Lab Synthet & Nat Funct Mol Chem,Minist Educ, Xian 710127, Shaanxi, Peoples R China
基金
中国博士后科学基金; 中国国家自然科学基金;
关键词
alkenes; cycloaddition; Diels-Alder reaction; dehydrogenation; NATURAL-PRODUCTS; DERIVATIVES; 1,3-DIENES; HYDROGEN; SERIES;
D O I
10.1002/adsc.201801436
中图分类号
O69 [应用化学];
学科分类号
081704 ;
摘要
A metal-free dehydrogenative Diels-Alder reaction of substituted alkenes for the synthesis of tetrahydroisoindolinones has been exploited for the first time. This new method features functional group tolerance and broad substrate scope, providing an efficient access to biologically active tetrahydroisoindolinone skeletons with endo steroselectivity in good to excellent yields.
引用
收藏
页码:2268 / 2273
页数:6
相关论文
共 57 条
[1]   Transition-Metal-Catalyzed Direct Arylation of (Hetero)Arenes by C-H Bond Cleavage [J].
Ackermann, Lutz ;
Vicente, Ruben ;
Kapdi, Anant R. .
ANGEWANDTE CHEMIE-INTERNATIONAL EDITION, 2009, 48 (52) :9792-9826
[2]   HIGHLY LIKE-SELECTIVE [4+2]-CYCLOADDITIONS OF CHIRAL DIENOLS - THE IMPORTANCE OF 1,3-ALLYLIC STRAIN IN THE HYDROXY-DIRECTED STEREOCONTROL [J].
ADAM, W ;
GLASER, J ;
PETERS, K ;
PREIN, M .
JOURNAL OF THE AMERICAN CHEMICAL SOCIETY, 1995, 117 (36) :9190-9193
[3]   Intermolecular oxidative cross-coupling of arenes [J].
Ashenhurst, James A. .
CHEMICAL SOCIETY REVIEWS, 2010, 39 (02) :540-548
[4]   Cross Dehydrogenative Coupling (CDC) Reactions of N,N-Disubstituted Formamides, Benzaldehydes and Cycloalkanes [J].
Batra, Aanchal ;
Singh, Paramjit ;
Singh, Kamal Nain .
EUROPEAN JOURNAL OF ORGANIC CHEMISTRY, 2016, 2016 (29) :4927-4947
[5]   The Pummerer reaction: Methodology and strategy for the synthesis of heterocyclic compounds [J].
Bur, SK ;
Padwa, A .
CHEMICAL REVIEWS, 2004, 104 (05) :2401-2432
[6]  
Corey EJ, 2002, ANGEW CHEM INT EDIT, V41, P1650, DOI 10.1002/1521-3773(20020517)41:10<1650::AID-ANIE1650>3.0.CO
[7]  
2-B
[8]  
Corey EJ, 1998, ANGEW CHEM INT EDIT, V37, P388, DOI 10.1002/(SICI)1521-3773(19980302)37:4<388::AID-ANIE388>3.0.CO
[9]  
2-V
[10]   Selective Catalytic Monoreduction of Phthalimides and Imidazolidine-2,4-diones [J].
Das, Shoubhik ;
Addis, Daniele ;
Knoepke, Leif R. ;
Bentrup, Ursula ;
Junge, Kathrin ;
Bruekner, Angelika ;
Beller, Matthias .
ANGEWANDTE CHEMIE-INTERNATIONAL EDITION, 2011, 50 (39) :9180-9184