Asymmetric allylation of aromatic aldehydes using chiral allylic tin reagents

被引:17
|
作者
Nishida, M
Tozawa, T
Yamada, K
Mukaiyama, T
机构
[1] Department of Applied Chemistry, Faculty of Science, Science University of Tokyo, Tokyo 162, Kagurazaka, Shinjuku-ku
关键词
D O I
10.1246/cl.1996.1125
中图分类号
O6 [化学];
学科分类号
0703 ;
摘要
Chiral allylating reagents, readily generated in situ from 2 lambda(2)-1,3,2-benzodioxastannole [Sn-II(O2C6H4)], allyl halides, chiral dialkyl tartrates and 1,8-diazabicyclo[5.4.0]-7-undecene (DBU) smoothly react with aromatic aldehydes at -78 degrees C in the presence of a catalytic amount of copper salts to afford the corresponding homoallylic alcohols in high yields with high enantioselectivities.
引用
收藏
页码:1125 / 1126
页数:2
相关论文
共 50 条
  • [1] Asymmetric allylation of carbonyl compounds with tartrate-modified chiral allylic tin reagents
    Yamada, K
    Tozawa, T
    Nishida, M
    Mukaiyama, T
    BULLETIN OF THE CHEMICAL SOCIETY OF JAPAN, 1997, 70 (09) : 2301 - 2308
  • [2] Asymmetric allylation of chiral aldehydes
    Elliott, EL
    McGarvey, GJ
    ABSTRACTS OF PAPERS OF THE AMERICAN CHEMICAL SOCIETY, 1996, 211 : 485 - CHED
  • [3] Asymmetric allylation of aldehydes with etherification by allyltrimethylsilane promoted by chiral alcohol modified aluminum reagents
    Yang, Y
    Wang, D
    PHOSPHORUS SULFUR AND SILICON AND THE RELATED ELEMENTS, 1998, 139 : 193 - 207
  • [4] ASYMMETRIC HYDROCYANATION OF ALDEHYDES USING CHIRAL TITANIUM REAGENTS
    MINAMIKAWA, H
    HAYAKAWA, S
    YAMADA, T
    IWASAWA, N
    NARASAKA, K
    BULLETIN OF THE CHEMICAL SOCIETY OF JAPAN, 1988, 61 (12) : 4379 - 4383
  • [5] Enantioselective allylation of aldehydes with chiral allyl organolanthanide reagents
    Qian, CT
    Huang, TS
    CHINESE JOURNAL OF CHEMISTRY, 1998, 16 (03) : 272 - 276
  • [6] Enantioselective allylation of aldehydes with chiral allyl organolanthanide reagents
    钱长涛
    黄太生
    ChineseJournalofChemistry, 1998, (03) : 272 - 276
  • [7] Enantioselective allylation of aldehydes promoted by chiral sulfur reagents
    Melo, RPA
    Vale, JA
    Zeni, G
    Menezes, PH
    TETRAHEDRON LETTERS, 2006, 47 (11) : 1829 - 1831
  • [8] New binuclear allylating reagents for allylation of aromatic aldehydes
    Wei Xiao-Ning
    Liu Ling-Yan
    Yu Lei
    Chang Wei-Xing
    Li Jing
    CHEMICAL JOURNAL OF CHINESE UNIVERSITIES-CHINESE, 2008, 29 (04): : 767 - 771
  • [9] New pyridine N-oxides as chiral organocatalysts in the asymmetric allylation of aromatic aldehydes
    Malkov, Andrei V.
    Westwater, Mary-Margaret
    Gutnov, Andrey
    Ramirez-Lopez, Pedro
    Friscourt, Frederic
    Kadlcikova, Aneta
    Hodacova, Jana
    Rankovic, Zoran
    Kotora, Martin
    Kocovsky, Pavel
    TETRAHEDRON, 2008, 64 (49) : 11335 - 11348
  • [10] Asymmetric allylation of aromatic aldehydes catalyzed by chiral phosphoramides prepared from (S)-proline
    Iseki, K
    Kuroki, Y
    Takahashi, M
    Kishimoto, S
    Kobayashi, Y
    TETRAHEDRON, 1997, 53 (10) : 3513 - 3526