Highly active and enantioselective copper-catalyzed conjugate addition of diethylzinc to cyclohexenone using sugar derivative diphosphites

被引：41
|
作者：
Pàmies, O [1 ]
Diéguez, M [1 ]
Net, G [1 ]
Ruiz, A [1 ]
Claver, C [1 ]
机构：
[1] Univ Rovira & Virgili, Dept Quim Fis & Inorgan, Tarragona 43005, Spain
来源：
TETRAHEDRON-ASYMMETRY | 2000年 / 11卷 / 21期
关键词：
D O I：
10.1016/S0957-4166(00)00430-4
中图分类号：
O61 [无机化学];
学科分类号：
070301 ; 081704 ;
摘要：
High enantioselectivity combined with unprecedented high catalytic activity (81% ee and TOF approximate to 1200 h(-1)) are achieved in the copper-catalyzed 1,4-addition of diethylzinc to 2-cyclohexenone with new C-1-chiral diphosphites derived from the readily available D-(+)-xylose. (C) 2000 Elsevier Science Ltd. All rights reserved.
引用
收藏
页码：4377 / 4383
页数：7
相关论文
共 50 条
  • [1] Highly enantioselective copper-catalyzed conjugate addition of diethylzinc to nitroalkenes
    Choi, H
    Hua, ZH
    Ojima, I
    ORGANIC LETTERS, 2004, 6 (16) : 2689 - 2691
  • [2] Chiral diphosphites derived from D-glucose in the copper-catalyzed conjugate addition of diethylzinc to cyclohexenone
    Diéguez, M
    Ruiz, A
    Claver, C
    TETRAHEDRON-ASYMMETRY, 2001, 12 (20) : 2895 - 2900
  • [3] Highly enantioselective copper-catalyzed conjugate addition of diethylzinc to nitroalkenes.
    Choi, HJ
    Hua, ZH
    Ojima, I
    ABSTRACTS OF PAPERS OF THE AMERICAN CHEMICAL SOCIETY, 2004, 228 : U35 - U35
  • [4] Highly enantioselective copper-catalyzed conjugate addition of diethylzinc to enones using chiral spiro phosphoramidites as ligands
    Zhou, H
    Wang, WH
    Fu, Y
    Xie, JH
    Shi, WJ
    Wang, LX
    Zhou, QL
    JOURNAL OF ORGANIC CHEMISTRY, 2003, 68 (04): : 1582 - 1584
  • [5] Highly enantioselective copper-catalyzed conjugate addition of diethylzinc to cyclic enones with spirocyclic phosphoramidite ligands
    Zhang, WC
    Wang, CJ
    Gao, WZ
    Zhang, XM
    TETRAHEDRON LETTERS, 2005, 46 (36) : 6087 - 6090
  • [6] Copper-catalyzed highly enantioselective 1,4-conjugate addition of trimethylaluminum to 2-cyclohexenone
    Liang, L
    Chan, ASC
    TETRAHEDRON-ASYMMETRY, 2002, 13 (13) : 1393 - 1396
  • [7] Enantioselective conjugate addition of diethylzinc to cyclohexenone catalyzed by a chiral aminophosphine-copper(II) triflate
    Mori, T
    Kosaka, K
    Nakagawa, Y
    Nagaoka, Y
    Tomioka, K
    TETRAHEDRON-ASYMMETRY, 1998, 9 (18) : 3175 - 3178
  • [8] 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
  • [9] Biphenol-based phosphoramidite ligands for the enantioselective copper-catalyzed conjugate addition of diethylzinc
    Alexakis, A
    Polet, D
    Rosset, S
    March, S
    JOURNAL OF ORGANIC CHEMISTRY, 2004, 69 (17): : 5660 - 5667
  • [10] Highly enantioselective copper-catalyzed 1,4-conjugate addition of diethylzinc to cyclic enones and α,β-unsaturated lactones
    Liang, L
    Yan, M
    Li, YM
    Chan, ASC
    TETRAHEDRON-ASYMMETRY, 2004, 15 (16) : 2575 - 2578
12345