Unmodified chiral primary amino alcohol as a new ligand for enantioselective alkynylation of aldehydes

被引:12
|
作者
Xu, Zhou [1 ]
Mao, Jincheng [1 ]
Zhang, Yawen [1 ]
机构
[1] Suzhou Univ, Coll Chem & Chem Engn, Key Lab Organ Synth Jiangsu Prov, Suzhou 215123, Peoples R China
关键词
Amino alcohol; Asymmetric alkynylation; Phenylacetylene; Enantioselectivity; Propargylic alcohols;
D O I
10.1016/j.catcom.2008.08.006
中图分类号
O64 [物理化学(理论化学)、化学物理学];
学科分类号
070304 ; 081704 ;
摘要
The unmodified available chiral amino alcohol 14 in combination with Ti((OPr)-Pr-i)(4) was found to catalyze the reaction of an alkynylzinc reagent with various aldehydes to generate chiral propargylic alcohols with moderate to good yields and enantioselectivities. (C) 2008 Elsevier B.V. All rights reserved.
引用
收藏
页码:113 / 117
页数:5
相关论文
共 50 条
  • [31] Boc-L-proline as a new chiral ligand for enantioselective phenylacetylene addition to aromatic aldehydes
    Zhou, YF
    Wang, R
    Xu, ZQ
    Yan, WJ
    Liu, L
    Gao, YF
    Da, CS
    TETRAHEDRON-ASYMMETRY, 2004, 15 (04) : 589 - 591
  • [32] 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
  • [33] Enantioselective alkynylation of aromatic ketones catalyzed by new chiral oxazolidine ligands
    Kang, YF
    Liu, L
    Wang, R
    Zhou, YF
    Yan, WJ
    ADVANCED SYNTHESIS & CATALYSIS, 2005, 347 (2-3) : 243 - 247
  • [34] Enantioselective alkynylation of aldehydes catalyzed by a camphor sulfonylated amino alcohols titanium(IV) catalyst system
    Gou, Shaohua
    Ye, Zhongbin
    Huang, Zhiyu
    Ma, Xiping
    APPLIED ORGANOMETALLIC CHEMISTRY, 2010, 24 (05) : 374 - 379
  • [35] Synthesis of new chiral aliphatic amino diselenides and their application as catalysts for the enantioselective addition of diethylzinc to aldehydes
    Braga, AL
    Paixao, MW
    LUdtke, DS
    Silveira, CC
    Rodrigues, OED
    ORGANIC LETTERS, 2003, 5 (15) : 2635 - 2638
  • [36] New polymer anchored chiral amino oxazolines as effective catalysts for enantioselective addition of diethylzinc to aldehydes
    Shaikh, NS
    Deshpande, VH
    Bedekar, AV
    TETRAHEDRON LETTERS, 2002, 43 (32) : 5587 - 5589
  • [37] Bicyclic and tricyclic compounds with beta-amino alcohol groups as chiral ligands in the enantioselective reaction of diethylzinc with aldehydes
    Aurich, HG
    Biesemeier, F
    Geiger, M
    Harms, K
    LIEBIGS ANNALEN-RECUEIL, 1997, (02): : 423 - 434
  • [38] ENANTIOSELECTIVE ADDITION OF DIETHYLZINC TO ALDEHYDES IN THE PRESENCE OF CHIRAL TITANIUM REAGENT MODIFIED WITH N-SULFONYLATED AMINO ALCOHOL
    ITO, K
    KIMURA, Y
    OKAMURA, H
    KATSUKI, T
    SYNLETT, 1992, (07) : 573 - 574
  • [39] ENANTIOSELECTIVE ALKYLATION OF ALDEHYDES CATALYZED BY NEW CHIRAL DISELENIDES
    WIRTH, T
    TETRAHEDRON LETTERS, 1995, 36 (43) : 7849 - 7852
  • [40] Effective activation of chiral BINOL/Ti(OiPr)4 catalyst with phenolic additives for the enantioselective alkynylation of aldehydes
    Lu, G
    Li, XS
    Chen, G
    Chan, WL
    Chan, ASC
    TETRAHEDRON-ASYMMETRY, 2003, 14 (04) : 449 - 452