Acyl-Imidazoles: A Privileged Ester Surrogate for Enantioselective Synthesis

被引：25

作者：

Lauberteaux, Jimmy ^{[1
]}

Pichon, Delphine ^{[2
]}

Basle, Olivier ^{[3
]}

Mauduit, Marc ^{[2
]}

Marcia de Figueiredo, Renata ^{[1
]}

Campagne, Jean-Marc ^{[1
]}

机构：

[1] Univ Montpellier, CNRS, UMR 5253, ICGM,ENSCM, 240 Ave Prof Emile Jeanbrau, F-34296 Montpellier 5, France

[2] Univ Rennes, Ecole Natl Super Chim Rennes, CNRS, UMR 6226,ISCR, 11 Allee Beaulieu,CS 50837, F-35708 Rennes 7, France

[3] CNRS, UPR 8241, Lab Chim Coordinat, 205 Route Narbonne, F-31077 Toulouse 4, France

来源：

CHEMCATCHEM | 2019年 / 11卷 / 23期

关键词：

acyl-imidazoles; versatile substrates; asymmetric synthesis; catalysis; post-functionalizations; ALPHA; BETA-UNSATURATED 2-ACYL IMIDAZOLES; ASYMMETRIC CONJUGATE ADDITION; METHYLIMIDAZOLE MICHAEL ACCEPTORS; ACTIVATED PHOTOREDOX CATALYSIS; FRIEDEL-CRAFTS ALKYLATIONS; COUPLED ELECTRON-TRANSFER; LEWIS-ACID; ALLYLIC ALKYLATION; KETONES; COMPLEX;

D O I：

10.1002/cctc.201900754

中图分类号：

O64 [物理化学（理论化学）、化学物理学];

学科分类号：

070304 ; 081704 ;

摘要：

Since the first report by Evans in asymmetric Friedel-Crafts reactions, the use of acyl-imidazoles has blossomed as powerful ester/amide surrogates. The imidazole scaffold indeed displays stability and special activation features allowing both better reactivity and selectivity in traditional ester/amide functionalizations: alpha-(enolate chemistry), beta-(conjugate additions), alpha,beta-(cycloadditions) or gamma/delta-(vinylogous). An overview of the contemporary and growing interest in acyl-imidazoles in metal- and organo-catalyzed transformations (bio-hybrid catalytic systems will be fully described in a back-to-back Minireview) will be highlighted. Moreover, post-functionalization expediencies are also going to be discussed in this Minireview.

引用

页码：5705 / 5722

页数：18

共 87 条

[1] Enantioselective CuII-Catalyzed Diels-Alder and Michael Addition Reactions in Water Using Bio-Inspired Triazacyclophane-Based Ligands [J].

Albada, H. Bauke ;

Rosati, Fiora ;

Coquiere, David ;

Roelfes, Gerard ;

Liskamp, Rob M. J. .

EUROPEAN JOURNAL OF ORGANIC CHEMISTRY, 2011, 2011 (09) :1714-1720

[2] Phase-transfer-catalyzed asymmetric acylimidazole alkylation [J].

Andrus, Merritt B. ;

Christiansen, Michael A. ;

Hicken, Erik J. ;

Gainer, Morgan J. ;

Bedke, D. Karl ;

Harper, Kaid C. ;

Mikkelson, Shawn R. ;

Dodson, Daniel S. ;

Harris, David T. .

ORGANIC LETTERS, 2007, 9 (23) :4865-4868

[3]

[Anonymous], 2010, ANGEW CHEM

[4]

[Anonymous], 2017, ANGEW CHEM, V129, P5760

[5]

Calvo BC, 2014, COPPER-CATALYZED ASYMMETRIC SYNTHESIS, P373

[6] Origins of Enantioselectivity in Asymmetric Radical Additions to Octahedral Chiral-at-Rhodium Enolates: A Computational Study [J].

Chen, Shuming ;

Huang, Xiaoqiang ;

Meggers, Eric ;

Houk, K. N. .

JOURNAL OF THE AMERICAN CHEMICAL SOCIETY, 2017, 139 (49) :17902-17907

[7] BOTPPI, a new Wittig salt for the synthesis of 12-(S)-hydroxy-eicosatetraenoic acid [12-(S)-HETE] [J].

Christiansen, Michael A. ;

Andrus, Merritt B. .

TETRAHEDRON LETTERS, 2012, 53 (36) :4805-4808

[8] Synthesis of Kurasoin B Using Phase-Transfer-Catalyzed Acylimidazole Alkylation [J].

Christiansen, Michael A. ;

Butler, Aaron W. ;

Hill, Amanda R. ;

Andrus, Merritt B. .

SYNLETT, 2009, (04) :653-657

[9] Visible-Light-Activated Catalytic Enantioselective β-Alkylation of α, β-Unsaturated 2-Acyl Imidazoles Using Hantzsch Esters as Radical Reservoirs [J].

de Assis, Francisco F. ;

Huang, Xiaoqiang ;

Akiyama, Midori ;

Pilli, Ronaldo A. ;

Meggers, Eric .

JOURNAL OF ORGANIC CHEMISTRY, 2018, 83 (18) :10922-10932

[10] Enantioselective conjugate addition of hydroxylamines to α,β-unsaturated 2-acyl imidazoles catalyzed by a chiral-at-metal Rh(III) complex [J].

Deng, Tao ;

Thota, Ganesh Kumar ;

Li, Yi ;

Kang, Qiang .

ORGANIC CHEMISTRY FRONTIERS, 2017, 4 (04) :573-577

← 1 2 3 4 5 6 7 8 9 →