New Approaches to Nitrogen Containing Heterocycles: Enantioselective Organocatalyzed Synthesis of Dihydropyridines (DHP's), Quinolizidine Derivatives and Dihydropyrimidines (DHPM's)

被引:0
作者
Hoai Thu Pham [1 ]
Chataigner, Isabelle [2 ]
Renaud, Jean-Luc [1 ]
机构
[1] Univ Caen ENSICAEN, UMR CNRS LCMT 6507, F-14050 Caen, France
[2] Univ Rouen, UMR CNRS COBRA 6014, F-76821 Mont St Aignan, France
关键词
Dihydropyridines; Dihydropyrimidines; Quinolizidines; Chiral Bronsted acids; Chiral thioureas; Proline type derivatives; CALCIUM-CHANNEL BLOCKERS; SOLVENT-FREE CONDITIONS; BETA-ENAMINO ESTERS; ONE-POT SYNTHESIS; BIGINELLI REACTION; BRONSTED ACID; ASYMMETRIC-SYNTHESIS; MICHAEL ADDITION; PICTET-SPENGLER; ALPHA; BETA-UNSATURATED ALDEHYDES;
D O I
10.2174/138527212802651322
中图分类号
O62 [有机化学];
学科分类号
070303 ; 081704 ;
摘要
Nitrogen-containing heterocycles, and more specifically the chiral ones, possess various biological and pharmaceutical properties. Among the approaches to these compounds, the organocatalyzed asymmetric multicomponent reaction has emerged as a powerful tool. This review will focus on the later development to chiral dihydropyridines, dihydropyrimidines and quinolizidines via asymmetric organocatalyzed synthesis.
引用
收藏
页码:1754 / 1775
页数:22
相关论文
共 119 条
[11]   Asymmetric catalysis with bifunctional cinchona alkaloid-based urea and thiourea organocatalysts [J].
Connon, Stephen J. .
CHEMICAL COMMUNICATIONS, 2008, (22) :2499-2510
[12]   The Design of Novel, Synthetically Useful (Thio)urea-Based Organocatalysts [J].
Connon, Stephen J. .
SYNLETT, 2009, (03) :354-376
[13]   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
[14]   Interaction of the mitotic inhibitor monastrol with human kinesin Eg5 [J].
DeBonis, S ;
Simorre, JP ;
Crevel, I ;
Lebeau, L ;
Skoufias, DA ;
Blangy, A ;
Ebel, C ;
Gans, P ;
Cross, R ;
Hackney, DD ;
Wade, RH ;
Kozielski, F .
BIOCHEMISTRY, 2003, 42 (02) :338-349
[15]   Primary Amine Catalyzed Biginelli Reaction for the Enantioselective Synthesis of 3,4-Dihydropyrimidin-2(1H)-ones [J].
Ding, Derong ;
Zhao, Cong-Gui .
EUROPEAN JOURNAL OF ORGANIC CHEMISTRY, 2010, 2010 (20) :3802-3805
[16]   Three-component Biginelli cyclocondensation reaction using C-glycosylated substrates.: Preparation of a collection of dihydropyrimidinone glycoconjugates and the synthesis of C-glycosylated monastrol analogues [J].
Dondoni, A ;
Massi, A ;
Sabbatini, S ;
Bertolasi, V .
JOURNAL OF ORGANIC CHEMISTRY, 2002, 67 (20) :6979-6994
[17]   Design and synthesis of new classes of Heterocyclic C-glycoconjugates and carbon-linked sugar and heterocyclic amino acids by asymmetric multicomponent reactions (AMCRs) [J].
Dondoni, Alessandro ;
Massi, Alessandro .
ACCOUNTS OF CHEMICAL RESEARCH, 2006, 39 (07) :451-463
[18]  
Dondoni A, 2003, MOL DIVERS, V6, P261
[19]   Small-molecule H-bond donors in asymmetric catalysis [J].
Doyle, Abigail G. ;
Jacobsen, Eric N. .
CHEMICAL REVIEWS, 2007, 107 (12) :5713-5743
[20]   RETRACTED: Enantioselective Organocatalytic Hantzsch Synthesis of Polyhydroquinolines (Retracted article. See vol. 23, pg. 3802, 2021) [J].
Evans, Christopher G. ;
Gestwicki, Jason E. .
ORGANIC LETTERS, 2009, 11 (14) :2957-2959