Pinacol coupling of benzaldehyde with TiCl2-amine

被引:0
|
作者
Matsubara, S [1 ]
Hashimoto, Y [1 ]
Okano, T [1 ]
Utimoto, K [1 ]
机构
[1] Kyoto Univ, Grad Sch Engn, Dept Chem Mat, Kyoto 6068501, Japan
关键词
titanium; pinacol; coupling; amine; asymmetric synthesis; diastereoselective synthesis;
D O I
暂无
中图分类号
O62 [有机化学];
学科分类号
070303 ; 081704 ;
摘要
A pinacol coupling of benzaldehyde with a homogeneous divalent titanium reagent, TiCl2-TMEDA-THF, gave the dl-hydrobenzoin with a high diastereoselectivity; by using an optically active amine instead of TMEDA, the reaction proceeded enantioselectively.
引用
收藏
页码:1411 / 1412
页数:2
相关论文
共 50 条
  • [21] Pinacol coupling of benzaldehydes mediated by titanium complexes displaying amine bis(phenolate) ligands
    Barroso, Sonia
    Adao, Pedro
    Coelho, Ana M.
    Pessoa, Joao Costa
    Martins, Ana M.
    JOURNAL OF MOLECULAR CATALYSIS A-CHEMICAL, 2016, 412 : 107 - 116
  • [22] On the paradox of TiCl4 reducing power:: pinacol coupling and two-carbon homologation of carbonyl compounds
    Clerici, A
    Pastori, N
    Porta, O
    TETRAHEDRON LETTERS, 2004, 45 (09) : 1825 - 1827
  • [23] Pinacol coupling of aromatic aldehydes and ketones mediated by TiCl4-Zn in ethyl acetate under ultrasound
    Li, Ji-Tai
    Sun, Xue-Li
    Lin, Zhi-Ping
    Chen, Yan-Xue
    Li, Toni-Shuang
    INDIAN JOURNAL OF CHEMISTRY SECTION B-ORGANIC CHEMISTRY INCLUDING MEDICINAL CHEMISTRY, 2007, 46 (08): : 1303 - 1307
  • [24] PINACOL COUPLING REACTIONS
    BUSMAN, M
    BRUSS, D
    FITZGERALD, A
    MUNDY, BP
    ABSTRACTS OF PAPERS OF THE AMERICAN CHEMICAL SOCIETY, 1987, 193 : 51 - ORGN
  • [25] Pinacol coupling of aromatic aldehydes and ketones using TiCl3-Al-EtOH under ultrasound irradiation
    Li, JT
    Lin, ZP
    Qi, N
    Li, TS
    SYNTHETIC COMMUNICATIONS, 2004, 34 (23) : 4339 - 4348
  • [26] Tuning selectivity among acetalization, pinacol coupling, and hydrogenation reactions of benzaldehyde by catalytic and photochemical pathways at room temperature
    Yang, Qingning
    Li, Xiyi
    Tang, Junwang
    MATERIALS TODAY ENERGY, 2022, 23
  • [27] TiCl4-n-Bu4NI as a reducing reagent:: Pinacol coupling and enolate formation from α-haloketones
    Tsuritani, T
    Ito, S
    Shinokubo, H
    Oshima, K
    JOURNAL OF ORGANIC CHEMISTRY, 2000, 65 (16): : 5066 - 5068
  • [28] The reaction of ketones with benzaldehyde catalyzed by TiCl4•2THF
    Tao, XC
    Liu, RZ
    Meng, QH
    Zhao, YY
    Zhou, YB
    Huang, JL
    JOURNAL OF MOLECULAR CATALYSIS A-CHEMICAL, 2005, 225 (02) : 239 - 243
  • [29] AMINE HYPOPHOSPHITE REACTIONS WITH BENZALDEHYDE
    TAUBE, DO
    VOVSI, BA
    IONIN, BI
    ZHURNAL OBSHCHEI KHIMII, 1972, 42 (02): : 351 - &
  • [30] STUDIES ON THE PINACOL COUPLING REACTION
    MUNDY, BP
    SRINIVASA, R
    KIM, Y
    DOLPH, T
    WARNET, RJ
    JOURNAL OF ORGANIC CHEMISTRY, 1982, 47 (09): : 1657 - 1661