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 50 条
  • [21] Enantioselective 1,4-addition of diarylphosphine oxides to α,β-unsaturated ketones catalyzed by oxazaborolidines
    Qian, Jinyi
    Zhao, Hengyuan
    Gao, Qi
    Chen, Lirong
    Shi, Yinrui
    Li, Jiuling
    Guo, Yafei
    Fan, Baomin
    ORGANIC CHEMISTRY FRONTIERS, 2023, 10 (22) : 5672 - 5679
  • [22] Recent Advances in Copper-Catalyzed Asymmetric Conjugate Addition of Grignard Reagents
    Tang, Fengxiang
    Ye, Jiuyong
    CHINESE JOURNAL OF ORGANIC CHEMISTRY, 2015, 35 (07) : 1414 - 1427
  • [23] ORGANOMANGANESE (II) REAGENTS .16. COPPER-CATALYZED 1,4-ADDITION OF ORGANOMANGANESE CHLORIDES TO CONJUGATED ENONES
    CAHIEZ, G
    ALAMI, M
    TETRAHEDRON LETTERS, 1989, 30 (27) : 3541 - 3544
  • [24] Copper-catalyzed highly enantioselective 1,4-conjugate addition of trimethylaluminum to 2-cyclohexenone
    Liang, L
    Chan, ASC
    TETRAHEDRON-ASYMMETRY, 2002, 13 (13) : 1393 - 1396
  • [25] The ortho effect:: copper-catalyzed highly enantioselective 1,4-conjugate addition of diethylzinc to chalcones
    Liu, LT
    Wang, MC
    Zhao, WX
    Zhou, YL
    Wang, XD
    TETRAHEDRON-ASYMMETRY, 2006, 17 (01) : 136 - 141
  • [26] Highly Enantioselective and Regioselective Copper-Catalyzed 1,4 Addition of Grignard Reagents to Cyclic Enynones
    Tissot, Matthieu
    Hernandez, Alexandra Perez
    Mueller, Daniel
    Mauduit, Marc
    Alexakis, Alexandre
    ORGANIC LETTERS, 2011, 13 (06) : 1524 - 1527
  • [27] Copper-catalyzed enantioselective 1,4-hydroboration of ?,?-unsaturated amides
    Yan, Hong-Hao
    Sha, Feng
    Wu, Xin-Yan
    TETRAHEDRON LETTERS, 2023, 117
  • [28] Chiral Sodium Phosphate Catalyzed Enantioselective 1,4-Addition of TMSCN to Aromatic Enones
    Yang, Jingya
    Wu, Shaoxiang
    Chen, Fu-Xue
    SYNLETT, 2010, (18) : 2725 - 2728
  • [29] Enantioselective 1,4-addition of cyclopropylboronic acid catalyzed by rhodium/chiral diene complexes
    Takechi, Ryosuke
    Nishimura, Takahiro
    CHEMICAL COMMUNICATIONS, 2015, 51 (40) : 8528 - 8531
  • [30] Enantioselective copper(I) catalyzed 1,4-addition of diethylzinc to cyclohexenone: asymmetric induction as an unexpected source of structural information
    Wendisch, V.
    Sewald, N.
    Tetrahedron: Asymmetry, 8 (08):