Catalytic Asymmetric Intramolecular Hydroacylation with Rhodium/Phosphoramidite-Alkene Ligand Complexes

被引:74
|
作者
Hoffman, Thomas J. [1 ]
Carreira, Erick M. [1 ]
机构
[1] ETH, Organ Chem Lab, CH-8093 Zurich, Switzerland
关键词
asymmetric catalysis; cyclopentanone; hydroacylation; P ligands; rhodium; CHIRAL DIENE LIGANDS; ENANTIOSELECTIVE CONJUGATE ADDITION; PHOSPHINE-OLEFIN COMPLEXES; TRANSITION-METAL CATALYSIS; PRIMARY ALLYLIC AMINES; STEERING LIGANDS; HOMOGENEOUS CATALYSIS; RHODIUM COMPLEXES; HIGH-PERFORMANCE; ORGANOSILICON COMPOUNDS;
D O I
10.1002/anie.201104595
中图分类号
O6 [化学];
学科分类号
0703 ;
摘要
Give me a P: An asymmetric intramolecular Rh-catalyzed hydroacylation reaction of pent-4-enals for the preparation of functionalized cyclopentanones in good yield and high enantioselectivity is described (see scheme, DCE=dichloroethane). This process uses rhodium complexes featuring novel modular phosphoramidite-alkene ligands and achiral phosphine coligands. Copyright © 2011 WILEY-VCH Verlag GmbH & Co. KGaA, Weinheim.
引用
收藏
页码:10670 / 10674
页数:5
相关论文
共 50 条
  • [41] cis-β-Bis(carbonyl) Ruthenium-Salen Complexes: X-ray Crystal Structures and Remarkable Catalytic Properties toward Asymmetric Intramolecular Alkene Cyclopropanation
    Xu, Zhen-Jiang
    Fang, Ran
    Zhao, Cunyuan
    Huang, Jie-Sheng
    Li, Gong-Yong
    Zhu, Nianyong
    Che, Chi-Ming
    JOURNAL OF THE AMERICAN CHEMICAL SOCIETY, 2009, 131 (12) : 4405 - 4417
  • [42] Synthesis of rhodium complexes of an asymmetric η5,η1,η1-cyclo-pentadienyl-bis(phosphine) ligand by regioselective intramolecular dehydrofluorinative C-C coupling
    Bellabarba, RM
    Nieuwenhuyzen, M
    Saunders, GC
    INORGANICA CHIMICA ACTA, 2001, 323 (1-2) : 78 - 88
  • [43] Dynamic, reactivity and catalytic behavior of pseudo-undercoordinated ruthenium and rhodium complexes stabilized by intramolecular solvents
    Lindner, E
    Pautz, S
    Haustein, M
    COORDINATION CHEMISTRY REVIEWS, 1996, 155 : 145 - 162
  • [44] ASYMMETRIC CATALYTIC REDUCTION WITH TRANSITION-METAL COMPLEXES .2. ASYMMETRIC CATALYSIS BY A SUPPORTED CHIRAL RHODIUM COMPLEX
    DUMONT, W
    POULIN, J
    DANG, T
    KAGAN, HB
    JOURNAL OF THE AMERICAN CHEMICAL SOCIETY, 1973, 95 (25) : 8295 - 8299
  • [45] Rhodium/Chiral Diene Complexes in the Catalytic Asymmetric Arylation of β-Pyrazol-1-yl Acrylates
    Gopula, Balraj
    Tsai, Yun-Fan
    Kuo, Ting-Shen
    Wu, Ping-Yu
    Henschke, Julian P.
    Wu, Hsyueh-Liang
    ORGANIC LETTERS, 2015, 17 (05) : 1142 - 1145
  • [46] Catalytic asymmetric synthesis of cyclopropane derivatives on chiral rhodium complexes - Isolation of carbene complex as intermediate
    Nishiyama, H
    ZHURNAL ORGANICHESKOI KHIMII, 1996, 32 (02): : 180 - 186
  • [47] Catalytic asymmetric hydrosilylation of ketones using rhodium-(I)-complexes of chiral phosphinooxazoline ligands
    Langer, T
    Janssen, J
    Helmchen, G
    TETRAHEDRON-ASYMMETRY, 1996, 7 (06) : 1599 - 1602
  • [48] [NO]- and [NN]-coordination mode rhodium complexes based on a flexible ligand: synthesis, reactivity and catalytic activity
    Yao, Zi-Jian
    Li, Kuan
    Zhang, Jian-Yong
    Deng, Wei
    NEW JOURNAL OF CHEMISTRY, 2016, 40 (10) : 8753 - 8759
  • [49] Asymmetric intramolecular cyclopropanation of diazo compounds with metallosalen complexes as catalyst: structural tuning of salen ligand
    Saha, B
    Uchida, T
    Katsuki, T
    TETRAHEDRON-ASYMMETRY, 2003, 14 (07) : 823 - 836