A highly enantioselective Bronsted acid catalyzed reaction cascade

被引:107
作者
Rueping, Magnus [1 ]
Antonchick, Andrey P. [1 ]
机构
[1] Goethe Univ Frankfurt, Inst Organ Chem & Chem Biol, D-60438 Frankfurt, Germany
关键词
Michael reaction; organocatalysis; phosphates; piperidines; reductive amination;
D O I
10.1002/anie.200801435
中图分类号
O6 [化学];
学科分类号
0703 ;
摘要
(Chemical Equation Presented) One cat. is enough! A highly enantiose-lective reaction has been developed for the three-component reaction of an enamine with a vinyl ketone and a Hantszsch ester in which each of the six reaction steps is catalyzed by the same chiral Brønsted acid (see scheme). This reaction offers efficient access to tetrahydropyridines and azadecalinones from simple and readily available starting materials. © 2008 Wiley-VCH Verlag GmbH & Co. KGaA.
引用
收藏
页码:5836 / 5838
页数:3
相关论文
共 93 条
[11]  
Bolm C, 2005, ANGEW CHEM, V117, P1788
[12]   Asymmetric synthesis of highly functionalized tetrahydrothiophenes by organocatalytic domino reactions [J].
Brandau, Sven ;
Maerten, Eddy ;
Jorgensen, Karl Anker .
JOURNAL OF THE AMERICAN CHEMICAL SOCIETY, 2006, 128 (46) :14986-14991
[13]  
CARLONE A, 2007, ANGEW CHEM, V119, P1119
[14]   A new approach for an organocatalytic multicomponent domino asymmetric reaction [J].
Carlone, Armando ;
Cabrera, Silvia ;
Marigo, Mauro ;
Jorgensen, Karl Anker .
ANGEWANDTE CHEMIE-INTERNATIONAL EDITION, 2007, 46 (07) :1101-1104
[15]   Highly enantioselective organocatalytic Biginelli reaction [J].
Chen, Xiao-Hua ;
Xu, Xiao-Ying ;
Liu, Hua ;
Cun, Lin-Feng ;
Gong, Liu-Zhu .
JOURNAL OF THE AMERICAN CHEMICAL SOCIETY, 2006, 128 (46) :14802-14803
[16]   Asymmetric organocatalytic reductions mediated by dihydropyridines [J].
Connon, Stephen J. .
ORGANIC & BIOMOLECULAR CHEMISTRY, 2007, 5 (21) :3407-3417
[17]   Alkaloids from amphibian skin: A tabulation of over eight-hundred compounds [J].
Daly, JW ;
Spande, TF ;
Garraffo, HM .
JOURNAL OF NATURAL PRODUCTS, 2005, 68 (10) :1556-1575
[18]   Thirty years of discovering arthropod alkaloids in amphibian skin [J].
Daly, JW .
JOURNAL OF NATURAL PRODUCTS, 1998, 61 (01) :162-172
[19]   Organocatalytic synthesis of drugs and bioactive natural products [J].
de Figueiredo, Renata Marcia ;
Christmann, Mathias .
EUROPEAN JOURNAL OF ORGANIC CHEMISTRY, 2007, 2007 (16) :2575-2600
[20]  
Enders D., 2007, Angew. Chem, V119, P1590, DOI DOI 10.1002/ange.200603129