Asymmetric catalysis.: Part 153:: Metal-catalysed enantioselective α-ketol rearrangement

被引：56
|
作者：
Brunner, H
Kagan, HB
Kreutzer, G
机构：
[1] Univ Regensburg, Inst Anorgan Chem, D-93040 Regensburg, Germany
[2] Univ Paris 11, Inst Chim Mol & Mat Orsay, F-91405 Orsay, France
来源：
TETRAHEDRON-ASYMMETRY | 2003年 / 14卷 / 15期
关键词：
D O I：
10.1016/S0957-4166(03)00433-6
中图分类号：
O61 [无机化学];
学科分类号：
070301 ; 081704 ;
摘要：
Promoted by catalytic amounts of Ni complexes tertiary alpha-hydroxyketones 1a, 3a-5a undergo rearrangement, forming chiral isomers 1b, 3b-5b. The best enantioselection was obtained with the model system 1-benzoylcyclopentanol 4a/2-hydroxy-2-phenylcyclohexanone 4b. In a ligand screening 2-[4-(S)-tert-butyloxazolin-2-yl]pyridine gave the highest enantiomeric excess of 46% (S)-4b. The analogous isomerisation reactions of alpha-hydroxyimines 6a, 7a forming chiral alpha-aminoketones 6b, 7b were established. (C) 2003 Elsevier Ltd. All rights reserved.
引用
收藏
页码：2177 / 2187
页数：11
相关论文
共 50 条
  • [41] Highly Enantioselective Cascade Transformations by Merging Heterogeneous Transition Metal Catalysis with Asymmetric Aminocatalysis
    Deiana, Luca
    Afewerki, Samson
    Palo-Nieto, Carlos
    Verho, Oscar
    Johnston, Eric V.
    Cordova, Armando
    SCIENTIFIC REPORTS, 2012, 2
  • [42] Homochiral porous metal-organic framework for highly enantioselective heterogeneous asymmetric catalysis
    Wu, CD
    Hu, A
    Zhang, L
    Lin, WB
    JOURNAL OF THE AMERICAN CHEMICAL SOCIETY, 2005, 127 (25) : 8940 - 8941
  • [43] Engineering Homochiral Metal-Organic Frameworks for Heterogeneous Asymmetric Catalysis and Enantioselective Separation
    Liu, Yan
    Xuan, Weimin
    Cui, Yong
    ADVANCED MATERIALS, 2010, 22 (37) : 4112 - 4135
  • [44] Highly Enantioselective Cascade Transformations by Merging Heterogeneous Transition Metal Catalysis with Asymmetric Aminocatalysis
    Luca Deiana
    Samson Afewerki
    Carlos Palo-Nieto
    Oscar Verho
    Eric V. Johnston
    Armando Córdova
    Scientific Reports, 2
  • [45] 1,1′-binaphthyiazepine-based ligands for asymmetric catalysis.: Part 2:: New aminoalcohols as chiral ligands in the enantioselective addition of ZnEt2 to aromatic aldehydes
    Superchi, S
    Mecca, T
    Giorgio, E
    Rosini, C
    TETRAHEDRON-ASYMMETRY, 2001, 12 (08) : 1235 - 1239
  • [46] Enantioselective catalysis - Part 124. Enantioselective Michael reaction catalyzed by optically active transition metal complexes
    Brunner, H
    Krumey, C
    JOURNAL OF MOLECULAR CATALYSIS A-CHEMICAL, 1999, 142 (01) : 7 - 15
  • [47] Montmorillonite clay catalysis. Part 8. Synthesis of arylcholestenes by Friedel-Crafts reaction catalysed by montmorillonite K-10.
    Li, LJ
    Lu, B
    Li, TS
    Li, JT
    SYNTHETIC COMMUNICATIONS, 1998, 28 (08) : 1439 - 1449
  • [48] Enantioselective Merger of Aminocatalysis with π-Lewis Acid Metal Catalysis: Asymmetric Preparation of Carbo- and Heterocycles
    Praveen, Chandrasekaran
    Montaignac, Benjamin
    Vitale, Maxime R.
    Ratovelomanana-Vidal, Virginie
    Michelet, Veronique
    CHEMCATCHEM, 2013, 5 (08) : 2395 - 2404
  • [49] Convergent Asymmetric Disproportionation Reactions: Metal/Bronsted Acid Relay Catalysis for Enantioselective Reduction of Quinoxalines
    Chen, Qing-An
    Wang, Duo-Sheng
    Zhou, Yong-Gui
    Duan, Ying
    Fan, Hong-Jun
    Yang, Yan
    Zhang, Zhang
    JOURNAL OF THE AMERICAN CHEMICAL SOCIETY, 2011, 133 (16) : 6126 - 6129
  • [50] Enantioselective catalysis.: Part 147.: A Rh(cod) complex with the chiral [Pt2S2{(-)diop}2] ligand
    Brunner, H
    Weber, M
    Zabel, M
    JOURNAL OF ORGANOMETALLIC CHEMISTRY, 2003, 684 (1-2) : 6 - 12
12345