Enantioselective N-Heterocyclic Carbene-Catalyzed Kinetic Resolution of Anilides

被引：48
作者：
Bie, Jianbo [1 ]
Lang, Ming [1 ]
Wang, Jian [1 ]
机构：
[1] Tsinghua Univ, Minist Educ, Sch Pharmaceut Sci, Key Lab Bioorgan Phosphorous Chem & Chem Biol, Beijing 100084, Peoples R China
来源：
ORGANIC LETTERS | 2018年 / 20卷 / 18期
基金：
中国国家自然科学基金;
关键词：
AXIALLY CHIRAL ANILIDES; NON-BIARYL ATROPISOMERS; DIELS-ALDER REACTION; ASYMMETRIC-SYNTHESIS; STEREOSELECTIVE-SYNTHESIS; EFFICIENT SYNTHESIS; SECONDARY ALCOHOLS; ENOLATE CHEMISTRY; STETTER REACTION; DRUG DISCOVERY;
D O I：
10.1021/acs.orglett.8b02538
中图分类号：
O62 [有机化学];
学科分类号：
070303 ; 081704 ;
摘要：
The N-heterocyclic carbene (NHC)-catalyzed enantioselective kinetic resolution of anilides (a kind of hemiaminals) is reported. Upon exposure to the reaction in the presence of an NHC precatalyst and base, catalytic C-O bond formation occurs, providing axially chiral isoindolinones in high yields with excellent enantioselectivities.
引用
收藏
页码：5866 / 5871
页数：6
相关论文
共 83 条
[1]   Synthesis of enantioenriched axially chiral anilides from atropisomerically enriched tartarate ortho-anilides [J].
Ates, A ;
Curran, DP .
JOURNAL OF THE AMERICAN CHEMICAL SOCIETY, 2001, 123 (21) :5130-5131
[2]   A novel asymmetric route to succinimides and derived compounds: synthesis of the lignan lactone (+)-hinokinin [J].
Bennett, DJ ;
Pickering, PL ;
Simpkins, NS .
CHEMICAL COMMUNICATIONS, 2004, (12) :1392-1393
[3]   Extending NHC-Catalysis: Coupling Aldehydes with Unconventional Reaction Partners [J].
Biju, Akkattu T. ;
Kuhl, Nadine ;
Glorius, Frank .
ACCOUNTS OF CHEMICAL RESEARCH, 2011, 44 (11) :1182-1195
[4]   Catalytic Kinetic Resolution of Cyclic Secondary Amines [J].
Binanzer, Michael ;
Hsieh, Sheng-Ying ;
Bode, Jeffrey W. .
JOURNAL OF THE AMERICAN CHEMICAL SOCIETY, 2011, 133 (49) :19698-19701
[5]   From a chiral switch to a ligand portfolio for asymmetric catalysis [J].
Blaser, Hans-Ulrich ;
Pugin, Benoit ;
Spindler, Felix ;
Thommen, Marc .
ACCOUNTS OF CHEMICAL RESEARCH, 2007, 40 (12) :1240-1250
[6]  
Blaser HU, 2002, ADV SYNTH CATAL, V344, P17, DOI 10.1002/1615-4169(200201)344:1<17::AID-ADSC17>3.0.CO
[7]  
2-8
[8]   Chirally aminated 2-naphthols-organocatalytic synthesis of non-biaryl atropisomers by asymmetric Friedel-Crafts amination [J].
Brandes, S ;
Bella, M ;
Kjoersgaard, A ;
Jorgensen, KA .
ANGEWANDTE CHEMIE-INTERNATIONAL EDITION, 2006, 45 (07) :1147-1151
[9]   Non-biaryl atropisomers in organocatalysis [J].
Brandes, Sebastian ;
Niess, Barbara ;
Bella, Marco ;
Prieto, Auxiliadora ;
Overgaard, Jacob ;
Jorgensen, Karl Anker .
CHEMISTRY-A EUROPEAN JOURNAL, 2006, 12 (23) :6039-6052
[10]   ON THE MECHANISM OF THIAMINE ACTION .4. EVIDENCE FROM STUDIES ON MODEL SYSTEMS [J].
BRESLOW, R .
JOURNAL OF THE AMERICAN CHEMICAL SOCIETY, 1958, 80 (14) :3719-3726
123456789