Enantioselective phenyl transfer to aldehydes using 1,1′-bi-2-naphthol-3,3′-dicarboxamide as chiral auxiliary

被引：36
作者：
Ito, K [1 ]
Tomita, Y
Katsuki, T
机构：
[1] Fukuoka Univ Educ, Dept Chem, Fukuoka 8114192, Japan
[2] Kyushu Univ 33, Fac Sci, Grad Sch, Dept Chem,Higashi Ku, Fukuoka 8128581, Japan
来源：
TETRAHEDRON LETTERS | 2005年 / 46卷 / 36期
基金：
日本科学技术振兴机构;
关键词：
zinc; asymmetric catalysis; 1,1 '-bi-2-naphthol; aryl transfer reaction;
D O I：
10.1016/j.tetlet.2005.06.161
中图分类号：
O62 [有机化学];
学科分类号：
070303 ; 081704 ;
摘要：
N,N.N'.N'-Tetra-n-butyl-BINOL-3,3'-dicarboxamide 5d was found to promote phenyl transfer from ethylphenylzinc to both aromatic and aliphatic aldehydes with high enantioselectivity up to 96% ee in tert-butyl methyl ether. (c) 2005 Elsevier Ltd. All rights reserved.
引用
收藏
页码：6083 / 6086
页数：4
相关论文
共 42 条
  • [31] Modular Phosphine-Aminophosphine Ligands Based on Chiral 1,2,3,4-Tetrahydro-1-naphthylamine Backbone: A New Class of Practical Ligands for Enantioselective Hydrogenations
    Qiu, Min
    Hu, Xiang-Ping
    Huang, Jia-Di
    Wang, Dao-Yong
    Deng, Jun
    Yu, Sai-Bo
    Duan, Zheng-Chao
    Zheng, Zhuo
    ADVANCED SYNTHESIS & CATALYSIS, 2008, 350 (17) : 2683 - 2689
  • [32] Enantioselective Michael reaction of 1,3-dicarbonyl compounds to 3-nitro-2H-chromenes catalyzed by chiral nickel complexes
    Chen, Wei-Yi
    Ouyang, Luo
    Chen, Rui-Ye
    Li, Xin-Sheng
    TETRAHEDRON LETTERS, 2010, 51 (30) : 3972 - 3974
  • [33] 1,1′-Binaphthalene-2-α-arylmethanol-2′-ols (Ar-BINMOLs) with Axial and sp3-Central Chirality: A Novel Chiral Ligands for Catalytic Asymmetric Transformations
    Zheng, Longsheng
    Song, Tao
    Xu, Liwen
    CHINESE JOURNAL OF ORGANIC CHEMISTRY, 2014, 34 (07) : 1255 - 1267
  • [34] Ir-Catalyzed Enantioselective Hydrogenation of 2H-1,4-Benzoxazines with a Chiral 1,2,3,4-Tetrahydro-1-naphthylamine Derived Phosphine-aminophosphine Ligand
    Hu Juan
    Wang Daoyong
    Zheng Zhuo
    Hu Xiangping
    CHINESE JOURNAL OF CHEMISTRY, 2012, 30 (11) : 2664 - 2668
  • [35] Chiral 1,2,3,4-tetrahydro-1-naphthylamine-derived phosphine-phosphoramidite ligand (THNAPhos): Application in highly enantioselective hydrogenations of functionalized C=C bonds
    Qiu, Min
    Hu, Xiang-Ping
    Wang, Dao-Yong
    Deng, Jun
    Huang, Jia-Di
    Yu, Sai-Bo
    Duan, Zheng-Chao
    Zheng, Zhuo
    ADVANCED SYNTHESIS & CATALYSIS, 2008, 350 (09) : 1413 - 1418
  • [36] Highly Enantioselective Copper(I)-Catalyzed Conjugate Addition of Terminal Alkynes to 1,1-Difluoro-1-(phenylsulfonyl)-3-en-2-ones: New Ester/Amide Surrogates in Asymmetric Catalysis
    Sanz-Marco, Amparo
    Garcia-Ortiz, Andrea
    Blay, Gonzalo
    Fernandez, Isabel
    Pedro, Jose R.
    CHEMISTRY-A EUROPEAN JOURNAL, 2014, 20 (03) : 668 - 672
  • [37] Acid-Catalyzed [3,3] Sigmatropic Rearrangement of N-Cbz-Diaryl Hydrazide for the Synthesis of Mono-N-Cbz-1,1′-biaryl-2,2′-diamine
    Suh, Sung-Eun
    Park, In-Keol
    Lim, Byeong-Yun
    Cho, Cheon-Gyu
    EUROPEAN JOURNAL OF ORGANIC CHEMISTRY, 2011, 2011 (03) : 455 - 457
  • [38] Enantioselective synthesis: of chiral γ-aryl α-keto ester by copper-catalyzed 1,4-conjugate addition using D2-symmetric biphenyl phosphoramidite ligand
    Yang, Bo
    Xie, Fang
    Yu, Han
    Shen, Kaiji
    Ma, Zhenni
    Zhang, Wanbin
    TETRAHEDRON, 2011, 67 (34) : 6197 - 6201
  • [39] Highly enantioselective hetero-Diels-Alder reaction between trans-1-methoxy-2-methyl-3-trimethylsiloxybuta-1,3-diene and aldehydes catalyzed by (R)-BINOL-Ti(IV) complex
    Gao, B
    Fu, ZY
    Yu, ZP
    Yu, L
    Huang, YZ
    Feng, XM
    TETRAHEDRON, 2005, 61 (24) : 5822 - 5830
  • [40] Enantioselective [3+2] annulation via C-H activation between cyclic N-acyl ketimines and 1,3-dienes catalyzed by iridium/chiral diene complexes
    Nishimura, Takahiro
    Nagamoto, Midori
    Ebe, Yusuke
    Hayashi, Tamio
    CHEMICAL SCIENCE, 2013, 4 (12) : 4499 - 4504
12345