Asymmetric organocatalytic cascade Michael/hemiketalization/retro-Henry reaction of β,γ-unsaturated ketoesters with α-nitroketones

被引:65
作者
Gao, Yaojun [1 ]
Ren, Qiao [1 ]
Siau, Woon-Yew [1 ]
Wang, Jian [1 ]
机构
[1] Natl Univ Singapore, Dept Chem, Singapore 117543, Singapore
关键词
FRIEDEL-CRAFTS ALKYLATION; C-H BONDS; ENANTIOSELECTIVE ADDITION; KINETIC RESOLUTION; MICHAEL ADDITION; CATALYSIS; DESYMMETRIZATION; COMPLEXES; THIOLS; ESTERS;
D O I
10.1039/c1cc11124h
中图分类号
O6 [化学];
学科分类号
0703 ;
摘要
An unprecedented enantioselective organocatalytic Michael/hemiketalization/retro-Henry cascade sequence is described, which catalyzed by a simple bifunctional indane amine-thiourea catalyst. This process provides a new route to the enantioselective synthesis of 5-nitro-pent-2-enoates, a precursor to alpha-ketolactam.
引用
收藏
页码:5819 / 5821
页数:3
相关论文
共 47 条
[1]   Asymmetric Formal trans-Dihydroxylation and trans-Aminohydroxylation of α,β-Unsaturated Aldehydes via an Organocatalytic Reaction Cascade [J].
Albrecht, Lukasz ;
Jiang, Hao ;
Dickmeiss, Gustav ;
Gschwend, Bjorn ;
Hansen, Signe Grann ;
Jorgensen, Karl Anker .
JOURNAL OF THE AMERICAN CHEMICAL SOCIETY, 2010, 132 (26) :9188-9196
[2]  
[Anonymous], 2008, Molecules that changed the world
[3]   Highly efficient dynamic kinetic resolution of azlactones by urea-based bifunctional organocatalysts [J].
Berkessel, A ;
Cleemann, F ;
Mukherjee, S ;
Müller, TN ;
Lex, J .
ANGEWANDTE CHEMIE-INTERNATIONAL EDITION, 2005, 44 (05) :807-811
[4]  
Berkessel A, 2005, ASYMMETRIC ORGANOCATALYSIS: FROM BIOMIMETIC CONCEPTS TO APPLICATIONS IN ASYMMETRIC SYNTHESIS, P1, DOI 10.1002/3527604677
[5]   Thiourea-Catalyzed Highly Enantio- and Diastereoselective Additions of Oxindoles to Nitroolefins: Application to the Formal Synthesis of (+)-Physostigmine [J].
Bui, Tommy ;
Syed, Salahuddin ;
Barbas, Carlos F., III .
JOURNAL OF THE AMERICAN CHEMICAL SOCIETY, 2009, 131 (25) :8758-+
[6]   ALTERING THE STEREOCHEMISTRY OF ALLYLATION REACTIONS OF CYCLIC ALPHA-SULFINYL RADICALS WITH DIARYLUREAS [J].
CURRAN, DP ;
KUO, LH .
JOURNAL OF ORGANIC CHEMISTRY, 1994, 59 (12) :3259-3261
[7]  
Dalko P.I., 2007, ENANTIOSELECTIVE ORG
[8]   Organocatalytic Asymmetric Desymmetrization-Fragmentation of Cyclic Ketones [J].
Dickmeiss, Gustav ;
De Sio, Vincenzo ;
Udmark, Jonas ;
Poulsen, Thomas B. ;
Marcos, Vanesa ;
Jorgensen, Karl Anker .
ANGEWANDTE CHEMIE-INTERNATIONAL EDITION, 2009, 48 (36) :6650-6653
[9]   A catalyst that plays multiple roles:: Asymmetric synthesis of β-substituted aspartic acid derivatives through a four-stage, one-pot procedure [J].
Dudding, T ;
Hafez, AM ;
Taggi, AE ;
Wagerle, TR ;
Lectka, T .
ORGANIC LETTERS, 2002, 4 (03) :387-390
[10]   Control of four stereocentres in a triple cascade organocatalytic reaction [J].
Enders, Dieter ;
Hüettl, Matthias R. M. ;
Grondal, Christoph ;
Raabe, Gerhard .
NATURE, 2006, 441 (7095) :861-863