Enantioselective addition of diethylzinc to aryl aldehydes catalyzed by 1,2,3,4-tetrahydroisoquinoline β-amino alcohol

被引：4
|
作者：
Xu, Geng
Liu, Zhan Zhu [1 ]
机构：
[1] Peking Union Med Coll, Inst Mat Med, Minist Educ, Key Lab Bioact Subst & Resources Utilizat Chinese, Beijing 100050, Peoples R China
来源：
CHINESE CHEMICAL LETTERS | 2010年 / 21卷 / 03期
关键词：
beta-Amino alcohol; Tetrahydroisoquinoline; Diethylzinc; Asymmetric addition; LIGAND;
D O I：
10.1016/j.cclet.2009.11.046
中图分类号：
O6 [化学];
学科分类号：
0703 ;
摘要：
A highly effective, new chiral 1,2,3,4-tetrahydroisoquinoline catalyst 1 for the diethylzinc addition to aryl aldehydes has been investigated. Using 10 mol% of this chiral catalyst, secondary alcohols can be obtained in up to 87% yield and 99.5% ee under mild conditions. (C) 2009 Zhan Zhu Liu. Published by Elsevier B.V. on behalf of Chinese Chemical Society. All rights reserved.
引用
收藏
页码：309 / 311
页数：3
相关论文
共 50 条
  • [21] Enantioselective addition of diethylzinc to aldehydes catalyzed by aziridine carbinols
    Wang, Xiaojuan
    Zhao, Wenxian
    Li, Gaowei
    Liu, Guanjun
    Wang, Jin
    Wang, Mincan
    Liu, Lantao
    TETRAHEDRON-ASYMMETRY, 2015, 26 (15-16) : 815 - 820
  • [22] Enantioselective addition of diethylzinc to aldehydes catalyzed by a new chiral β-amino alcohol derived from D-mannitol
    Cho, BT
    Chun, YS
    TETRAHEDRON-ASYMMETRY, 1998, 9 (09) : 1489 - 1492
  • [23] SYNTHESIS AND PHARMACOLOGICAL CHARACTERIZATION OF 1-PHENYL-1,2,3,4-TETRAHYDROISOQUINOLINE, 4-PHENYL-1,2,3,4-TETRAHYDROISOQUINOLINE, AND 1-BENZYL-1,2,3,4-TETRAHYDROISOQUINOLINE AS DOPAMINE RECEPTOR LIGANDS
    CHARIFSON, PS
    WYRICK, SD
    HOFFMAN, AJ
    SIMMONS, RMA
    BOWEN, JP
    MCDOUGALD, DL
    MAILMAN, RB
    JOURNAL OF MEDICINAL CHEMISTRY, 1988, 31 (10) : 1941 - 1946
  • [24] Asymmetric addition of diethylzinc to aldehydes catalyzed by a camphor-derived β-amino alcohol
    Wu, Zhi-Long
    Wu, Hsyueh-Liang
    Wu, Ping-Yu
    Uang, Biing-Jiun
    TETRAHEDRON-ASYMMETRY, 2009, 20 (13) : 1556 - 1560
  • [25] The application of chiral aminonaphthols in the enantioselective addition of diethylzinc to aryl aldehydes
    Liu, DX
    Zhang, LC
    Wang, Q
    Da, CS
    Xin, ZQ
    Wang, R
    Choi, MCK
    Chan, ASC
    ORGANIC LETTERS, 2001, 3 (17) : 2733 - 2735
  • [26] Enantioselective addition of diethylzinc to aldehydes catalyzed by polymer-supported chiral amino thioacetates
    Kim, YM
    Jin, MJ
    BULLETIN OF THE KOREAN CHEMICAL SOCIETY, 2004, 25 (06): : 775 - 776
  • [27] Anticancer activity of ruthenium(II) arene complexes bearing 1,2,3,4-tetrahydroisoquinoline amino alcohol ligands
    Chelopo, Madichaba P.
    Pawar, Sachin A.
    Sokhela, Mxolisi K.
    Govender, Thavendran
    Kruger, Hendrik G.
    Maguire, Glenn E. M.
    EUROPEAN JOURNAL OF MEDICINAL CHEMISTRY, 2013, 66 : 407 - 414
  • [28] SYNTHESIS AND ACYLATION OF 1,2,3,4-TETRAHYDROISOQUINOLINE DERIVATIVES
    MIKHAILOVSKY, AG
    ALEXANDROV, BB
    VAKHRIN, MI
    KHIMIYA GETEROTSIKLICHESKIKH SOEDINENII, 1993, (06): : 780 - 783
  • [29] 1,2,3,4-TETRAHYDROISOQUINOLINE DERIVATIVES WITH ANTIHYPERTENSIVE PROPERTIES
    WENNER, W
    JOURNAL OF MEDICINAL CHEMISTRY, 1965, 8 (01) : 125 - &
  • [30] ENANTIOSELECTIVE ADDITION OF DIETHYLZINC TO ALDEHYDES CATALYZED BY CHIRAL HYDROXY AMINAL
    ASAMI, M
    INOUE, S
    CHEMISTRY LETTERS, 1991, (04) : 685 - 688
12345