Recent advances in enantioselective copper-catalyzed 1,4-addition

被引:311
作者
Jerphagnon, Thomas [1 ]
Pizzuti, M. Gabriella [1 ]
Minnaard, Adriaan J. [1 ]
Feringa, Ben L. [1 ]
机构
[1] Univ Groningen, Stratingh Inst Chem, NL-9747 AG Groningen, Netherlands
关键词
ASYMMETRIC CONJUGATE ADDITION; QUATERNARY STEREOGENIC CENTERS; CHIRAL PHOSPHORUS LIGANDS; ALKOXY-NHC LIGANDS; DIALKYLZINC REAGENTS; GRIGNARD-REAGENTS; CYCLIC ENONES; ALPHA; BETA-UNSATURATED KETONES; ORGANOMETALLIC REAGENTS; ORGANOZINC REAGENTS;
D O I
10.1039/b816853a
中图分类号
O6 [化学];
学科分类号
0703 ;
摘要
A comprehensive overview of recent literature from 2003 concerning advances in enantioselective copper catalysed 1,4-addition of organometallic reagents to alpha,beta-unsaturated compounds is given in this critical review. About 200 ligands and catalysts are presented, with a focus on stereoselectivities, catalyst loading, ligand structure and substrate scope. A major part is devoted to trapping and tandem reactions and a variety of recent synthetic applications are used to illustrate the practicality and current state of the art of 1,4-addition of organometallic reagents. Finally several mechanistic studies are discussed (162 references).
引用
收藏
页码:1039 / 1075
页数:37
相关论文
共 250 条
[1]  
Abele S, 2000, EUR J ORG CHEM, V2000, P1
[2]   Copper-catalyzed tandem conjugate addition-electrophilic trapping: Ketones, esters, and nitriles as terminal electrophiles [J].
Agapiou, K ;
Cauble, DF ;
Krische, MJ .
JOURNAL OF THE AMERICAN CHEMICAL SOCIETY, 2004, 126 (14) :4528-4529
[3]   Two birds with one metallic stone: Single-pot catalysis of fundamentally different transformations [J].
Ajamian, A ;
Gleason, JL .
ANGEWANDTE CHEMIE-INTERNATIONAL EDITION, 2004, 43 (29) :3754-3760
[4]   Enantioselective copper-catalyzed conjugate addition and allylic substitution reactions [J].
Alexakis, A. ;
Backvall, J. E. ;
Krause, N. ;
Pamies, O. ;
Dieguez, M. .
CHEMICAL REVIEWS, 2008, 108 (08) :2796-2823
[5]   Highly enantioselective copper(I)-phosphoramidite-catalysed additions of organoaluminium reagents to enones [J].
Alexakis, A ;
Albrow, V ;
Biswas, K ;
d'Augustin, M ;
Prieto, O ;
Woodward, S .
CHEMICAL COMMUNICATIONS, 2005, (22) :2843-2845
[6]   Biphenol-based phosphoramidite ligands for the enantioselective copper-catalyzed conjugate addition of diethylzinc [J].
Alexakis, A ;
Polet, D ;
Rosset, S ;
March, S .
JOURNAL OF ORGANIC CHEMISTRY, 2004, 69 (17) :5660-5667
[7]   Biphenol-based ligands for Cu-catalyzed asymmetric conjugate addition [J].
Alexakis, A ;
Polet, D ;
Benhaim, C ;
Rosset, S .
TETRAHEDRON-ASYMMETRY, 2004, 15 (14) :2199-2203
[8]   Asymmetric synthesis with N-heterocyclic carbenes.: Application to the copper-catalyzed conjugate addition [J].
Alexakis, A ;
Winn, CL ;
Guillen, F ;
Pytkowicz, J ;
Roland, S ;
Mangeney, P .
ADVANCED SYNTHESIS & CATALYSIS, 2003, 345 (03) :345-348
[9]   Tandem enantioselective conjugate addition-cyclopropanation. Application to natural products synthesis [J].
Alexakis, A ;
March, S .
JOURNAL OF ORGANIC CHEMISTRY, 2002, 67 (25) :8753-8757
[10]  
Alexakis A, 2000, EUR J ORG CHEM, V2000, P4011, DOI 10.1002/1099-0690(200012)2000:24<4011::AID-EJOC4011>3.0.CO