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
[21]   NHC-Cu-Catalyzed Enantioselective Hydroboration of Acyclic and Exocyclic 1,1-Disubstituted Aryl Alkenes [J].
Corberan, Rosa ;
Mszar, Nicholas W. ;
Hoveyda, Amir H. .
ANGEWANDTE CHEMIE-INTERNATIONAL EDITION, 2011, 50 (31) :7079-7082
[22]   Highly regioselective decarboxylative Claisen rearrangement reactions of diallyl 2-sulfonylmalonates [J].
Craig, Donald ;
Lansdell, Mark I. ;
Lewis, Simon E. .
TETRAHEDRON LETTERS, 2007, 48 (44) :7861-7864
[23]   Convenient catalytic, enantioselective conjugate reduction of nitroalkenes using CuF2 [J].
Czekelius, C ;
Carreira, EM .
ORGANIC LETTERS, 2004, 6 (24) :4575-4577
[24]   Catalytic enantioselective conjugate reduction of β,β-disubstituted nitroalkenes [J].
Czekelius, C ;
Carreira, EM .
ANGEWANDTE CHEMIE-INTERNATIONAL EDITION, 2003, 42 (39) :4793-4795
[25]   Enantioselective reduction of nitroalkene mixtures by in situ equilibration [J].
Czekelius, Constantin ;
Carreira, Erick M. .
ORGANIC PROCESS RESEARCH & DEVELOPMENT, 2007, 11 (03) :633-636
[27]   Evaluation of (+)-sparteine-like diamines for asymmetric synthesis [J].
Dearden, MJ ;
McGrath, MJ ;
O'Brien, P .
JOURNAL OF ORGANIC CHEMISTRY, 2004, 69 (17) :5789-5792
[28]   Enantioselective synthesis of β-aryl-γ-amino acid derivatives via Cu-catalyzed asymmetric 1,4-reductions of γ-phthalimido-substituted α,β-unsaturated carboxylic acid esters [J].
Deng, Jun ;
Hu, Xiang-Ping ;
Huang, Jia-Di ;
Yu, Sai-Bo ;
Wang, Dao-Yong ;
Duan, Zheng-Chao ;
Zheng, Zhuo .
JOURNAL OF ORGANIC CHEMISTRY, 2008, 73 (15) :6022-6024
[29]   Catalytic enantioselective reduction of β,β-disubstituted vinyl phenyl Sulfones by using bisphosphine monoxide Ligands [J].
Desrosiers, Jean-Nicolas ;
Charette, Andre B. .
ANGEWANDTE CHEMIE-INTERNATIONAL EDITION, 2007, 46 (31) :5955-5957
[30]   CuH-catalyzed reactions [J].
Deutsch, Carl ;
Krause, Norbert ;
Lipshutz, Bruce H. .
CHEMICAL REVIEWS, 2008, 108 (08) :2916-2927