Asymmetric pinacol coupling of aromatic aldehydes with TiCl2/enantiopure amine or hydrazine reagents

被引：45
|
作者：
Enders, D [1 ]
Ullrich, EC [1 ]
机构：
[1] Rhein Westfal TH Aachen, Inst Organ Chem, D-52074 Aachen, Germany
来源：
TETRAHEDRON-ASYMMETRY | 2000年 / 11卷 / 19期
关键词：
D O I：
10.1016/S0957-4166(00)00379-7
中图分类号：
O61 [无机化学];
学科分类号：
070301 ; 081704 ;
摘要：
Asymmetric pinacol coupling of aromatic aldehydes under homogeneous conditions with TiCl2 in the presence of enantiopure amines or hydrazines afforded 1,2-diols in moderate to excellent yields with good dl-diastereoselectivities and enantioselectivities in the range of 6-65% ee. A non-linear temperature effect ('principle of isoinversion') has been examined. (C) 2000 Elsevier Science Ltd. All rights reserved.
引用
收藏
页码：3861 / 3865
页数：5
相关论文
共 50 条
  • [31] Studies on the neodymium-induced pinacol coupling of aromatic aldehydes and ketones in aqueous media
    Bian, Yan Jiang
    Wang, Hai Long
    Wu, Bo
    Li, Ji Tai
    CHINESE CHEMICAL LETTERS, 2006, 17 (05) : 591 - 594
  • [32] Studies on the Neodymium-induced Pinacol Coupling of Aromatic Aldehydes and Ketones in Aqueous Media
    Yan Jiang BIAN1*
    Chinese Chemical Letters, 2006, (05) : 591 - 594
  • [33] Magnesium-induced pinacol coupling of aromatic aldehydes and ketones under ultrasound irradiation
    Wang, JS
    Li, JT
    Lin, ZP
    Li, TS
    SYNTHETIC COMMUNICATIONS, 2005, 35 (10) : 1419 - 1424
  • [34] Studies on the lanthanum-induced pinacol coupling of aromatic aldehydes and ketones in aqueous media
    Bian, Yan-Jiang
    Yu, Xu-Guang
    Peng, Hong-Wei
    Li, Ji-Tai
    SYNTHETIC COMMUNICATIONS, 2006, 36 (17) : 2513 - 2518
  • [35] Asymmetric allylation of aromatic aldehydes using chiral allylic tin reagents
    Nishida, M
    Tozawa, T
    Yamada, K
    Mukaiyama, T
    CHEMISTRY LETTERS, 1996, (12) : 1125 - 1126
  • [36] Pinacol coupling of aromatic aldehydes mediated by Zn in aqueous oxalic acid under ultrasound irradiation
    Li, JT
    Chen, YX
    Yang, JH
    Li, TS
    JOURNAL OF CHEMICAL RESEARCH, 2004, (07) : 494 - 495
  • [37] Pinacol coupling of aromatic aldehydes catalysed by a titanocene complex: A transition metal catalysed radical reaction
    Gansauer, A
    CHEMICAL COMMUNICATIONS, 1997, (05) : 457 - 458
  • [38] Tandem pinacol coupling - rearrangement of aromatic aldehydes with hydrogen catalyzed by a combination of a platinum complex and a polyoxometalate
    Branytska, Olena
    Shimon, Linda J. W.
    Neumann, Ronny
    CHEMICAL COMMUNICATIONS, 2007, (38) : 3957 - 3959
  • [39] Pinacol coupling of aromatic aldehydes and ketones using magnesium in aqueous ammonium chloride under ultrasound
    Li, JT
    Bian, YJ
    Zang, HJ
    Li, TS
    SYNTHETIC COMMUNICATIONS, 2002, 32 (04) : 547 - 551
  • [40] Reductive Coupling of Aromatic Aldehydes and Acetophenone Induced by TiCl4-Al/CH2(COOEt)2
    Song, Chang-Ying
    Wang, Shu-Xiang
    Chu, Wen-Hao
    Li, Ji-Tai
    Zhou, Zheng
    Li, Hong-Yu
    Cao, Zi-Qing
    ASIAN JOURNAL OF CHEMISTRY, 2013, 25 (14) : 7993 - 7996
12345