Asymmetric bis(alkoxycarbonylation) reaction of homoallylic alcohols catalyzed by palladium in the presence of Cu(I) triflate using the chiral bioxazoline ligand

被引：42
|
作者：
Ukaji, Y
Miyamoto, M
Mikuni, M
Takeuchi, S
Inomata, K
机构：
[1] Department of Chemistry, Faculty of Science, Kanazawa University, Kakuma, Kanazawa
来源：
BULLETIN OF THE CHEMICAL SOCIETY OF JAPAN | 1996年 / 69卷 / 03期
关键词：
D O I：
10.1246/bcsj.69.735
中图分类号：
O6 [化学];
学科分类号：
0703 ;
摘要：
Palladium-catalyzed asymmetric intra- and intermolecular bis(alkoxycarbonylation) reactions of homoallylic alcohols in the presence of copper(I) triflate were achieved by using the chiral bioxazoline ligand, (S,S)-4,4'-dibenzyl-4,4',5,5'-tetrahydro-2,2'-bioxazole, under normal pressure of carbon monoxide and oxygen at 25 degrees C to give the corresponding optically active gamma-butyrolactones in 19-65% ee.
引用
收藏
页码：735 / 742
页数：8
相关论文
共 50 条
  • [1] Asymmetric bis(alkoxycarbonylation) reaction of terminal olefins catalyzed by palladium in the presence of copper(I) triflate and a chiral bioxazoline ligand
    Takeuchi, S
    Ukaji, Y
    Inomata, K
    BULLETIN OF THE CHEMICAL SOCIETY OF JAPAN, 2001, 74 (05) : 955 - 958
  • [2] Asymmetric bis(alkoxycarbonylation) reaction of cyclic olefins catalyzed by palladium in the presence of copper(I) triflate
    Aratani, Takahiro
    Tahara, Kenji
    Takeuchi, Susumu
    Ukaji, Yutaka
    Inomata, Katsuhiko
    CHEMISTRY LETTERS, 2007, 36 (11) : 1328 - 1329
  • [3] Asymmetric Bis(alkoxycarbonylation) Reaction of Cyclic Olefins Catalyzed by Palladium in the Presence of Copper(I) Triflate
    Aratani, Takahiro
    Tahara, Kenji
    Takeuchi, Susumu
    Kitamura, Satoko
    Murai, Moemi
    Fujinami, Shuhei
    Inomata, Katsuhiko
    Ukaji, Yutaka
    BULLETIN OF THE CHEMICAL SOCIETY OF JAPAN, 2012, 85 (11) : 1225 - 1232
  • [4] Ring-opening Bis(alkoxycarbonylation) Reaction of Methylenecyclopropanes Catalyzed by Palladium in the Presence of Copper(I) Salt
    Aratani, Takahiro
    Ukaji, Yutaka
    Inomata, Katsuhiko
    CHEMISTRY LETTERS, 2009, 38 (01) : 46 - 47
  • [5] From allylic alcohols to chiral tertiary homoallylic alcohol: palladium-catalyzed asymmetric allylation of isatins
    Qiao, Xiang-Chen
    Zhu, Shou-Fei
    Zhou, Qi-Lin
    TETRAHEDRON-ASYMMETRY, 2009, 20 (11) : 1254 - 1261
  • [6] CATALYZED ASYMMETRIC REACTION OF ALDEHYDES WITH DIALKYLZINC IN THE PRESENCE OF CHIRAL PYRIDYL ALCOHOLS AS LIGANDS
    ISHIZAKI, M
    FUJITA, K
    SHIMAMOTO, M
    HOSHINO, O
    TETRAHEDRON-ASYMMETRY, 1994, 5 (03) : 411 - 424
  • [7] Desymmetrization of meso-methylenecyclopropanes by a palladium-catalyzed asymmetric ring-opening bis(alkoxycarbonylation) reaction
    Yonezawa, Yasushi
    Furuya, Tomoki
    Aratani, Takahiro
    Fijinami, Shuhei
    Inomata, Katsuhiko
    Ukaji, Yutaka
    TETRAHEDRON-ASYMMETRY, 2014, 25 (12) : 936 - 943
  • [8] SELECTIVE MONO(ALKOXYCARBONYLATION) AND BIS(ALKOXYCARBONYLATION) OF OLEFINS CATALYZED BY PALLADIUM IN THE PRESENCE OF CU(I) OR CU(II) CHLORIDE UNDER REMARKABLY MILD CONDITIONS - APPLICATION TO THE SYNTHESIS OF GAMMA-BUTYROLACTONE DERIVATIVES
    TODA, S
    MIYAMOTO, M
    KINOSHITA, H
    INOMATA, K
    BULLETIN OF THE CHEMICAL SOCIETY OF JAPAN, 1991, 64 (12) : 3600 - 3606
  • [9] A Chiral Bis(arsine) Ligand: Synthesis and Applications in Palladium-Catalyzed Asymmetric Allylic Alkylations
    Uberman, Paula M.
    Caira, Mino R.
    Martin, Sandra E.
    ORGANOMETALLICS, 2013, 32 (11) : 3220 - 3226
  • [10] Asymmetric Henry reaction catalyzed by Cu(I)-based chiral amino alcohol complex
    Shen, Tianhua
    Qin, Quan
    Ni, Hang
    Xia, Ting
    Zhou, Xiaocong
    Cui, Funa
    Li, Junqi
    Ran, Deqiang
    Song, Qingbao
    TURKISH JOURNAL OF CHEMISTRY, 2013, 37 (06) : 966 - 977
12345