Enantioselective alkynylation of aromatic ketones catalyzed by new chiral oxazolidine ligands

被引：60
|
作者：
Kang, YF
Liu, L
Wang, R
Zhou, YF
Yan, WJ
机构：
[1] Chinese Acad Sci, Lanzhou Inst Chem Phys, State Key Lab Oxo Synth & Select Oxidat, Lanzhou 730000, Gansu, Peoples R China
[2] Lanzhou Univ, Sch Life Sci, Dept Biochem & Mol Biol, Lanzhou 730000, Peoples R China
来源：
ADVANCED SYNTHESIS & CATALYSIS | 2005年 / 347卷 / 2-3期
关键词：
addition to ketones; alkynes; asymmetric catalysis; C-C bond formation; oxazolidines; propargylic alcohols;
D O I：
10.1002/adsc.200404278
中图分类号：
O69 [应用化学];
学科分类号：
081704 ;
摘要：
New chiral oxazolidine ligands have been derived conveniently from natural amino acids in good yields. Their use in the enantioselective addition of phenylacetylene to aromatic ketones has been tested with the best ee being up to 88%. We provide a simple, practical and inexpensive method to generate chiral tertiary propargylic alcohols.
引用
收藏
页码：243 / 247
页数：5
相关论文
共 50 条
  • [1] Enantioselective alkynylation of aromatic aldehydes catalyzed by new chiral oxazolidine ligands
    Kang, YF
    Wang, R
    Liu, L
    Da, CS
    Yan, WJ
    Xu, ZQ
    TETRAHEDRON LETTERS, 2005, 46 (05) : 863 - 865
  • [2] Enantioselective alkynylation of aromatic ketones catalyzed by chiral camphorsulfonamide ligands
    Lu, G
    Li, XS
    Jia, X
    Chan, WL
    Chan, ASC
    ANGEWANDTE CHEMIE-INTERNATIONAL EDITION, 2003, 42 (41) : 5057 - 5058
  • [3] Enantioselective alkynylation of aromatic aldehydes catalyzed by new chiral amino alcohol-based ligands
    Lu, G
    Li, XS
    Zhou, ZY
    Chan, WL
    Chan, ASC
    TETRAHEDRON-ASYMMETRY, 2001, 12 (15) : 2147 - 2152
  • [4] Enantioselective Alkynylation of Trifluoromethyl Ketones Catalyzed by Chiral Schiff Bases
    Dhayalan, Vasudevan
    Murakami, Ryo
    Hayashi, Masahiko
    ASIAN JOURNAL OF CHEMISTRY, 2013, 25 (13) : 7505 - 7508
  • [5] Enantioselective addition of diethylzinc to aromatic aldehydes catalyzed by new chiral oxazolidine ligand
    Kang, YF
    Liu, L
    Wang, R
    Ni, M
    Han, ZJ
    SYNTHETIC COMMUNICATIONS, 2005, 35 (13) : 1819 - 1823
  • [6] Sulfamide-amine alcohol catalyzed enantioselective alkynylation of aromatic ketones
    Mao, JC
    Wan, BS
    Wu, F
    Lu, SW
    JOURNAL OF MOLECULAR CATALYSIS A-CHEMICAL, 2005, 237 (1-2) : 126 - 131
  • [7] Enantioselective alkynylation of aromatic aldehydes catalyzed by readily available chiral amino alcohol-based ligands
    Li, Z
    Upadhyay, V
    DeCamp, AE
    DiMichele, L
    Reider, PJ
    SYNTHESIS-STUTTGART, 1999, : 1453 - 1458
  • [8] Enantioselective alkynylation of aldehydes catalyzed by new chiral catalysts
    Chan, ASC
    Lu, G
    Li, XS
    METHODOLOGIES IN ASYMMETRIC CATALYSIS, 2004, 880 : 103 - 113
  • [9] Highly enantioselective alkynylation of aldehydes catalyzed by a new oxazolidine-titanium complex
    Xu, Zhou
    Mao, Jincheng
    Zhang, Yawen
    ORGANIC & BIOMOLECULAR CHEMISTRY, 2008, 6 (07) : 1288 - 1292
  • [10] Enantioselective Direct Alkynylation of Ketones Catalyzed by Chiral CCN Pincer RhIII Complexes
    Ito, Jun-ichi
    Ubukata, Shino
    Muraoka, Shun
    Nishiyama, Hisao
    CHEMISTRY-A EUROPEAN JOURNAL, 2016, 22 (47) : 16800 - 16803
12345