C=N-Containing Azaarenes as Activating Groups in Enantioselective Catalysis

被引:127
作者
Best, Daniel
Lam, Hon Wai [1 ]
机构
[1] Univ Edinburgh, Sch Chem, EaStCHEM, Edinburgh EH9 3JJ, Midlothian, Scotland
基金
英国工程与自然科学研究理事会;
关键词
ASYMMETRIC CONJUGATE ADDITION; FRIEDEL-CRAFTS ALKYLATION; POTASSIUM TERT-BUTOXIDE; N-SULFONYL ALDIMINES; 1,3-DICARBONYL COMPOUNDS; MICHAEL ADDITION; CINNAMYL DERIVATIVES; ARYLBORONIC ACIDS; VINYL KETONES; REDUCTION;
D O I
10.1021/jo402414k
中图分类号
O62 [有机化学];
学科分类号
070303 ; 081704 ;
摘要
Nitrogen-containing aromatic heterocycles (azaarenes) are of widespread chemical significance, and chiral compounds containing azaarenes feature prominently in pharmaceuticals, agrochemicals, and natural products. This Perspective highlights the use of a relatively underdeveloped strategy to prepare chiral azaarene-containing compounds: exploitation of the C=N bond embedded within certain azaarenes to activate adjacent functionality in catalytic asymmetric reactions. Work in this area has resulted in the development of several different types of catalytic enantio-selective processes, including reductions, nucleophilic additions, and reductive couplings. It is hoped that this Perspective will encourage more researchers to work in this promising area.
引用
收藏
页码:831 / 845
页数:15
相关论文
共 157 条
[1]   Vinylogous nitroaldol (Henry) reaction using 3,5-diethyl-4-nitroisoxazole and carbonyl compounds [J].
Adamo, Mauro F. A. ;
Suresh, Surisetti .
TETRAHEDRON, 2009, 65 (05) :990-997
[2]   New studies of Rh-catalyzed addition of boronic acids under basic conditions in aqueous medium [J].
Amengual, R ;
Michelet, V ;
Genêt, JP .
TETRAHEDRON LETTERS, 2002, 43 (34) :5905-5908
[3]   Novel bifunctional chiral urea and thiourea derivatives as organocatalysts:: Enantioselective nitro-Michael reaction of malonates and diketones [J].
Andres, Jose M. ;
Manzano, Ruben ;
Pedrosa, Rafael .
CHEMISTRY-A EUROPEAN JOURNAL, 2008, 14 (17) :5116-5119
[4]  
[Anonymous], ORGANOLITHIUMS SELEC
[5]   SYNTHESIS OF PYRIMIDOBLAMIC ACID AND EPIPYRIMIDOBLAMIC ACID [J].
AOYAGI, Y ;
CHORGHADE, MS ;
PADMAPRIYA, AA ;
SUGUNA, H ;
HECHT, SM .
JOURNAL OF ORGANIC CHEMISTRY, 1990, 55 (26) :6291-6298
[6]   Asymmetric conjugate reduction of α,β-unsaturated esters using a chiral phosphine-copper catalyst [J].
Appella, DH ;
Moritani, Y ;
Shintani, R ;
Ferreira, EM ;
Buchwald, SL .
JOURNAL OF THE AMERICAN CHEMICAL SOCIETY, 1999, 121 (40) :9473-9474
[7]   Catalytic Functionalization of Indoles in a New Dimension [J].
Bandini, Marco ;
Eichholzer, Astrid .
ANGEWANDTE CHEMIE-INTERNATIONAL EDITION, 2009, 48 (51) :9608-9644
[8]   Development of a catalytic enantioselective conjugate addition of 1,3-dicarbonyl compounds to nitroalkenes for the synthesis of endothelin-A antagonist ABT-546. Scope, mechanism, and further application to the synthesis of the antidepressant rolipram [J].
Barnes, DM ;
Ji, JG ;
Fickes, MG ;
Fitzgerald, MA ;
King, SA ;
Morton, HE ;
Plagge, FA ;
Preskill, M ;
Wagaw, SH ;
Wittenberger, SJ ;
Zhang, J .
JOURNAL OF THE AMERICAN CHEMICAL SOCIETY, 2002, 124 (44) :13097-13105
[9]   THE REACTION OF ISOPROPYLLITHIUM AND TERT-BUTYLLITHIUM WITH SIMPLE OLEFINS [J].
BARTLETT, PD ;
FRIEDMAN, S ;
STILES, M .
JOURNAL OF THE AMERICAN CHEMICAL SOCIETY, 1953, 75 (07) :1771-1772
[10]   ETHYLENATION OF SECONDARY AND TERTIARY ALKYLLITHIUMS .I. CONDITIONS AND LIMITS OF REACTION [J].
BARTLETT, PD ;
TAUBER, SJ ;
WEBER, WP .
JOURNAL OF THE AMERICAN CHEMICAL SOCIETY, 1969, 91 (23) :6362-&