Chiral Gold Complex-Catalyzed Hetero-Diels-Alder Reaction of Diazenes: Highly Enantioselective and General for Dienes

被引：66
作者：
Liu, Bin
Li, Kang-Nan
Luo, Shi-Wei
Huang, Jian-Zhou
Pang, Huan
Gong, Liu-Zhu [1 ]
机构：
[1] Univ Sci & Technol China, Hefei Natl Lab Phys Sci Microscale, Hefei 230026, Peoples R China
来源：
JOURNAL OF THE AMERICAN CHEMICAL SOCIETY | 2013年 / 135卷 / 09期
关键词：
ALPHA-L-FUCOSIDASES; CARBONYL-COMPOUNDS; SELECTIVE INHIBITORS; CYCLIZATION; CYCLOADDITIONS; CYCLOISOMERIZATION; PIPERAZIMYCIN; CHEMISTRY; ALDEHYDES; LIGANDS;
D O I：
10.1021/ja3110472
中图分类号：
O6 [化学];
学科分类号：
0703 ;
摘要：
A chiral gold(I) complex-catalyzed highly regio- and enantioselective azo hetero-Diels-Alder reaction has been developed. The chiral gold(I) complex acting as a Lewis acid exhibits high efficiency in the activation of urea-based diazene dienophiles. Moreover, this chiral gold catalyst also rendered a cascade intramolecular enyne cycloisomerization/asymmetric azo-HDA reaction.
引用
收藏
页码：3323 / 3326
页数：4
相关论文
共 50 条
[1]   Catalytic and enantioselective aza-ene and hetero-Diels-Alder reactions of alkenes and dienes with azodicarboxylates [J].
Aburel, PS ;
Zhuang, W ;
Hazell, RG ;
Jorgensen, KA .
ORGANIC & BIOMOLECULAR CHEMISTRY, 2005, 3 (12) :2344-2349
[2]  
Albini A., 1976, THEORETICAL INORGANI, P105
[3]   Gold-Catalyzed [4C+2C] Cycloadditions of Allenedienes, including an Enantioselective Version with New Phosphoramidite-Based Catalysts: Mechanistic Aspects of the Divergence between [4C+3C] and [4C+2C] Pathways [J].
Alonso, Isaac ;
Trillo, Beatriz ;
Lopez, Fernando ;
Montserrat, Sergi ;
Ujaque, Gregori ;
Castedo, Luis ;
Lledos, Agusti ;
Mascarenas, Jose L. .
JOURNAL OF THE AMERICAN CHEMICAL SOCIETY, 2009, 131 (36) :13020-13030
[4]   Alternative synthetic methods through new developments in catalysis by gold [J].
Arcadi, Antonio .
CHEMICAL REVIEWS, 2008, 108 (08) :3266-3325
[5]   Dual Hard/Soft Gold Catalysis: Intermolecular Friedel-Crafts-Type α-Amidoalkylation/Alkyne Hydroarylation Sequences by N-Acyliminium Ion Chemistry [J].
Boiaryna, Liliana ;
El Mkaddem, Mohamed Kamal ;
Taillier, Catherine ;
Dalla, Vincent ;
Othman, Mohamed .
CHEMISTRY-A EUROPEAN JOURNAL, 2012, 18 (44) :14192-14200
[6]   On the mechanism of the puzzling "Endocyclic" skeletal rearrangement of 1,6-enynes [J].
Cabello, Noemi ;
Jimenez-Nunez, Eloisa ;
Bunuel, Elena ;
Cardenas, Diego J. ;
Echavarren, Antonio M. .
EUROPEAN JOURNAL OF ORGANIC CHEMISTRY, 2007, 2007 (25) :4217-4223
[7]   ANTIPROLIFERATIVE EFFECTS OF INHIBITORS OF POLYAMINE SYNTHESIS IN TUMORS OF NEURAL ORIGIN [J].
CHAPMAN, SK ;
GLANT, SK .
JOURNAL OF PHARMACEUTICAL SCIENCES, 1980, 69 (06) :733-735
[8]   Gold(I)-Catalyzed Cycloisomerization of β-Alkynylpropiolactones to Substituted α-Pyrones [J].
Dombray, Thomas ;
Blanc, Aurelien ;
Weibel, Jean-Marc ;
Pale, Patrick .
ORGANIC LETTERS, 2010, 12 (23) :5362-5365
[9]   Synthesis of (2S,5S)-5-fluoromethylornithine; A potent inhibitor of ornithine aminotransferase [J].
Ducep, JB ;
Heintzelmann, B ;
Jund, K ;
Lesur, B ;
Schleimer, M ;
Zimmermann, PR .
TETRAHEDRON-ASYMMETRY, 1997, 8 (02) :327-335
[10]   Axially Chiral Triazoloisoquinolin-3-ylidene Ligands in Gold(I)-Catalyzed Asymmetric Intermolecular (4+2) Cycloadditions of Allenamides and Dienes [J].
Francos, Javier ;
Grande-Carmona, Francisca ;
Faustino, Helio ;
Iglesias-Sigueenza, Javier ;
Diez, Elena ;
Alonso, Isaac ;
Fernandez, Rosario ;
Lassaletta, Jose M. ;
Lopez, Fernando ;
Mascarenas, Jose L. .
JOURNAL OF THE AMERICAN CHEMICAL SOCIETY, 2012, 134 (35) :14322-14325
12345