Investigation of a novel diamine based chiral auxiliary in the asymmetric alkylation of ketones

被引:7
|
作者
Clarke, Sarah L.
McSweeney, Christina M.
McGlacken, Gerard P. [1 ]
机构
[1] Natl Univ Ireland Univ Coll Cork, Analyt & Biol Chem Res Facil, Cork, Ireland
基金
爱尔兰科学基金会;
关键词
IONOPHORE ANTIBIOTIC X-14547A; CYCLIC CARBAMATE HYDRAZONES; ALPHA-ALKYLATION; ACYCLIC KETONES; PROLINE; ALPHA; ALPHA-BISALKYLATION; TETRAHYDROPYRAN; DERIVATIVES; EFFICIENT;
D O I
10.1016/j.tetasy.2014.01.006
中图分类号
O61 [无机化学];
学科分类号
070301 ; 081704 ;
摘要
A novel chiral auxiliary containing a pyrrolidine ring has been utilised in the preparation of various chiral ketones with good to excellent enantioselectivities (up to 92%). It has been successfully employed in aldol and Michael reactions giving moderate to high selectivity. (C) 2014 Elsevier Ltd. All rights reserved.
引用
收藏
页码:356 / 361
页数:6
相关论文
共 50 条
  • [1] New Chiral Norbornenesultam as the Chiral Auxiliary in Asymmetric Alkylation
    W.H.Chan
    A.W.M.Lee
    厦门大学学报(自然科学版), 1999, (S1) : 211 - 211
  • [2] BINAPHTHOL AS A CHIRAL AUXILIARY - ASYMMETRIC ALKYLATION OF ARYLACETIC ACID
    FUJI, K
    NODE, M
    TANAKA, F
    HOSOI, S
    TETRAHEDRON LETTERS, 1989, 30 (21) : 2825 - 2828
  • [3] Asymmetric transfer hydrogenation of ketones with a polymer-supported chiral diamine
    Li, XG
    Chen, WP
    Hems, W
    King, F
    Xiao, JL
    TETRAHEDRON LETTERS, 2004, 45 (05) : 951 - 953
  • [4] Cyclosulfamide as a chiral auxiliary: application to efficient asymmetric synthesis (alkylation/aldolization)
    Fecourt, Fabien
    Lopez, Gerald
    Van Der Lee, Arie
    Martinez, Jean
    Dewynter, Georges
    TETRAHEDRON-ASYMMETRY, 2010, 21 (19) : 2361 - 2366
  • [5] Novel dendritic ligands of chiral 1,2-diamine and their application in asymmetric hydrogenation of simple aryl ketones
    Liu, WG
    Cui, X
    Cun, LF
    Wu, J
    Zhu, J
    Deng, JG
    Fan, QH
    SYNLETT, 2005, (10) : 1591 - 1595
  • [6] Asymmetric transfer hydrogenation of ketones and imines with novel water-soluble chiral diamine as ligand in neat water
    Li, Li
    Wu, Jiashou
    Wang, Fei
    Liao, Jian
    Zhang, Hua
    Lian, Chunxia
    Zhu, Jin
    Deng, Jingen
    GREEN CHEMISTRY, 2007, 9 (01) : 23 - 25
  • [7] Synthesis of (+)-siphonarienone: Asymmetric alkylation using a chiral benzopyrano-isoxazolidine auxiliary
    Abiko, A
    Masamune, S
    TETRAHEDRON LETTERS, 1996, 37 (07) : 1081 - 1084
  • [9] New chiral rhodium and iridium complexes with chiral diamine ligands for asymmetric transfer hydrogenation of aromatic ketones
    Murata, K
    Ikariya, T
    JOURNAL OF ORGANIC CHEMISTRY, 1999, 64 (07): : 2186 - 2187
  • [10] ASYMMETRIC SYNTHESIS OF ALPHA-SUBSTITUTED KETONES BY METALATION AND ALKYLATION OF CHIRAL HYDRAZONES
    ENDERS, D
    EICHENAUER, H
    ANGEWANDTE CHEMIE-INTERNATIONAL EDITION IN ENGLISH, 1976, 15 (09): : 549 - 551