Enantioselective N-H Insertion Reaction of a-Aryl a-Diazoketones: An Efficient Route to Chiral a- Aminoketones

被引:114
作者
Xu, Bin [1 ,2 ,3 ]
Zhu, Shou-Fei [1 ,2 ,3 ]
Zuo, Xiao-Dong [1 ,2 ,3 ]
Zhang, Zhi-Chao [1 ,2 ,3 ]
Zhou, Qi-Lin [1 ,2 ,3 ]
机构
[1] Nankai Univ, State Key Lab, Tianjin 300071, Peoples R China
[2] Nankai Univ, Inst Elementoorgan Chem, Tianjin 300071, Peoples R China
[3] Collaborat Innovat Ctr Chem Sci & Engn, Tianjin, Peoples R China
基金
中国国家自然科学基金;
关键词
asymmetric catalysis; carbenes; chiral proton shuttle; chiral; -aminoketones; diazo compounds; INITIATED CLAISEN REARRANGEMENT; SPIRO PHOSPHORIC-ACIDS; CATALYZED TANDEM YLIDE; ALPHA-DIAZO KETONES; DONOR/ACCEPTOR CARBENOIDS; ASYMMETRIC-SYNTHESIS; INTRAMOLECULAR CYCLOPROPANATION; BOND INSERTIONS; RHODIUM; DERIVATIVES;
D O I
10.1002/anie.201400236
中图分类号
O6 [化学];
学科分类号
0703 ;
摘要
A highly enantioselective NH insertion reaction of -diazoketones was developed by using cooperative catalysis by dirhodium(II) carboxylates and chiral spiro phosphoric acids. The insertion reaction provides a new access route to diverse chiral -aminoketones, which are versatile building blocks in organic synthesis, with fast reaction rates, good yields and high enantioselectivity under mild and neutral conditions.
引用
收藏
页码:3913 / 3916
页数:4
相关论文
共 63 条
[11]   Enantiocontrol in intramolecular cyclopropanation of diazoketones. Conformational control of metal carbene alignment [J].
Doyle, MP ;
Eismont, MY ;
Zhou, QL .
RUSSIAN CHEMICAL BULLETIN, 1997, 46 (05) :955-958
[12]   Novel aminopropiophenones as potential antidepressants [J].
Foley, KF ;
Cozzi, NV .
DRUG DEVELOPMENT RESEARCH, 2003, 60 (04) :252-260
[13]   Amino acid derived thiane oxide and dioxide systems as disposable templates: Synthesis of alpha-amino ketones, anti-amino alcohols and an amino cyclopentenone [J].
Gamble, MP ;
Giblin, GMP ;
Montana, JG ;
OBrien, P ;
Ockendon, TP ;
Taylor, RJK .
TETRAHEDRON LETTERS, 1996, 37 (41) :7457-7460
[14]   A method for the catalytic enantioselective synthesis of 6-silylated 2-cyclohexenones [J].
Ge, M ;
Corey, EJ .
TETRAHEDRON LETTERS, 2006, 47 (14) :2319-2321
[15]   BF3•OEt2-Mediated Highly Regioselective SN2-Type Ring-Opening of N-Activated Aziridines and N-Activated Azetidines by Tetraalkylammonium Halides [J].
Ghorai, Manas K. ;
Kumar, Amit ;
Tiwari, Deo Prakash .
JOURNAL OF ORGANIC CHEMISTRY, 2010, 75 (01) :137-151
[16]   Trapping of oxonium ylide with isatins: Efficient and stereoselective construction of adjacent quaternary carbon centers [J].
Guo, Xin ;
Huang, Haoxi ;
Yang, Liping ;
Hu, Wenhao .
ORGANIC LETTERS, 2007, 9 (23) :4721-4723
[17]   Novel Multicomponent Reactions via Trapping of Protic Onium Ylides with Electrophiles [J].
Guo, Xin ;
Hu, Wenhao .
ACCOUNTS OF CHEMICAL RESEARCH, 2013, 46 (11) :2427-2440
[18]   Asymmetric imino aza-enamine reaction catalyzed by axially chiral dicarboxylic acid:: Use of arylaldehyde N,N-dialkylhydrazones as acyl anion equivalent [J].
Hashimoto, Takuya ;
Hirose, Maya ;
Maruoka, Keiji .
JOURNAL OF THE AMERICAN CHEMICAL SOCIETY, 2008, 130 (24) :7556-+
[19]  
Hou Z., 2010, Angew. Chem., V122, P4873
[20]   Highly Enantioselective Insertion of Carbenoids into N-H Bonds Catalyzed by Copper(I) Complexes of Binol Derivatives [J].
Hou, Zongrui ;
Wang, Jun ;
He, Peng ;
Wang, Jing ;
Qin, Bo ;
Liu, Xiaohua ;
Lin, Lili ;
Feng, Xiaoming .
ANGEWANDTE CHEMIE-INTERNATIONAL EDITION, 2010, 49 (28) :4763-4766