Catalytic asymmetric allylation of aldehydes via a chiral indium(III) complex

被引:66
|
作者
Teo, YC [1 ]
Tan, KT [1 ]
Loh, TP [1 ]
机构
[1] Natl Univ Singapore, Dept Chem, Singapore 117543, Singapore
关键词
D O I
10.1039/b412736f
中图分类号
O6 [化学];
学科分类号
0703 ;
摘要
A chiral indium complex has been discovered to effect high enantioselectivities in the addition of allyltributyl stannanes to aldehydes. The allylation of a variety of aromatic, alpha,beta-unsaturated and aliphatic aldehydes resulted in good yields and high enantioselectivities ( 90 - 96% ee).
引用
收藏
页码:1318 / 1320
页数:3
相关论文
共 50 条
  • [31] Catalytic asymmetric carbonyl allylation mediated by palladium and indium.
    Cook, GR
    Sun, LD
    ABSTRACTS OF PAPERS OF THE AMERICAN CHEMICAL SOCIETY, 2003, 225 : U286 - U286
  • [32] Asymmetric catalytic cyanosilylation of aldehydes using a chiral binaphthol-titanium complex
    Mori, M
    Imma, H
    Nakai, T
    TETRAHEDRON LETTERS, 1997, 38 (35) : 6229 - 6232
  • [33] Asymmetric allylation of aromatic aldehydes using chiral allylic tin reagents
    Nishida, M
    Tozawa, T
    Yamada, K
    Mukaiyama, T
    CHEMISTRY LETTERS, 1996, (12) : 1125 - 1126
  • [34] Asymmetric α-Allylation of Aldehydes with Alkynes by Integrating Chiral Hydridopalladium and Enamine Catalysis
    Su, Yong-Liang
    Li, Lu-Lu
    Zhou, Xiao-Le
    Dai, Zhen-Yao
    Wang, Pu-Sheng
    Gong, Liu-Zhu
    ORGANIC LETTERS, 2018, 20 (08) : 2403 - 2406
  • [35] Asymmetric allyltributylstannane addition to ketones catalyzed by chiral indium(III)-PYBOX complex
    Lu Jun
    Ji Shun-Jun
    CHINESE JOURNAL OF CHEMISTRY, 2006, 24 (10) : 1439 - 1442
  • [36] On the mechanism of catalytic, enantioselective allylation of aldehydes with chlorosilanes and chiral Lewis bases
    Denmark, SE
    Fu, JP
    JOURNAL OF THE AMERICAN CHEMICAL SOCIETY, 2000, 122 (48) : 12021 - 12022
  • [37] Barbier allylation of aldehydes and ketones with aluminium and catalytic indium metal: an economical alternative
    Preite, Marcelo D.
    Jorquera-Geroldi, Hugo A.
    Perez-Carvajal, Andres
    ARKIVOC, 2011, : 380 - 388
  • [38] Asymmetric catalytic alkylation of aldehydes with diethylzinc using a chiral binaphthol-titanium complex
    Mori, M
    Nakai, T
    TETRAHEDRON LETTERS, 1997, 38 (35) : 6233 - 6236
  • [39] Asymmetric Carbonyl Allylation of Aldehydes with Allylic Alcohols under the Sequential Catalysis of Palladium Complex and Chiral Phosphoric Acid
    Zhang Zi-Jing
    Tao Zhong-Lin
    Adele, Arafate
    Gong Liu-Zhu
    ACTA CHIMICA SINICA, 2017, 75 (12) : 1196 - 1201
  • [40] New chiral bis-titanium(IV) catalyst with dibenzofuran spacer for catalytic asymmetric allylation of aldehydes and aryl ketones
    Hanawa, H
    Kii, S
    Maruoka, K
    ADVANCED SYNTHESIS & CATALYSIS, 2001, 343 (01) : 57 - 60