New and improved ligands for highly enantioselective catalytic diphenylzinc additions to aryl aldehydes

被引:86
|
作者
Huang, WS [1 ]
Pu, L [1 ]
机构
[1] Univ Virginia, Dept Chem, Charlottesville, VA 22901 USA
关键词
D O I
10.1016/S0040-4039(99)02041-9
中图分类号
O62 [有机化学];
学科分类号
070303 ; 081704 ;
摘要
By introducing electron-withdrawing fluorine atoms to a chiral 1,1'-binaphthyl ligand (R)-1, a new catalyst (S)-5d has been obtained which shows improved catalytic properties for the asymmetric diphenylzinc addition to aldehydes. This new ligand allows the synthesis of chiral diarylcarbinols with high enantioselectivity in shorter reaction time under simple reaction conditions. (C) 1999 Elsevier Science Ltd. All rights reserved.
引用
收藏
页码:145 / 149
页数:5
相关论文
共 50 条
  • [41] A new ligand scaffold for catalytic asymmetric alkylzinc additions to aldehydes
    Wipf, P
    Wang, XD
    ORGANIC LETTERS, 2002, 4 (07) : 1197 - 1200
  • [42] Computer assisted design: Ligands for highly enantioselective addition of diethyl zinc to aldehydes
    Pericas, MA
    Vidal-Ferran, A
    Sola, L
    Reddy, KS
    Vazquez, A
    Moyano, A
    Riera, A
    ABSTRACTS OF PAPERS OF THE AMERICAN CHEMICAL SOCIETY, 1998, 216 : U511 - U511
  • [43] Highly efficient synthesis of enantiomerically pure (S)-2-amino-1,2,2-triphenylethanol.: Development of a new family of ligands for the highly enantioselective catalytic ethylation of aldehydes
    Reddy, KS
    Solà, L
    Moyano, A
    Pericàs, MA
    Riera, A
    JOURNAL OF ORGANIC CHEMISTRY, 1999, 64 (11): : 3969 - 3974
  • [44] Application of a new family of P,N ligands to the highly enantioselective hydrosilylation of aryl alkyl and dialkyl ketones
    Tao, BT
    Fu, GC
    ANGEWANDTE CHEMIE-INTERNATIONAL EDITION, 2002, 41 (20) : 3892 - 3894
  • [45] Catalytic enantioselective arylation of aldehydes:: boronic acids as a suitable source of transferable aryl groups
    Braga, AL
    Lüdtke, DS
    Vargas, F
    Paixao, MW
    CHEMICAL COMMUNICATIONS, 2005, (19) : 2512 - 2514
  • [46] Catalytic Enantioselective Synthesis of Diarylmethanols from Aryl Bromides and Aldehydes by Using Organolithium Reagents
    Nakagawa, Yuya
    Muramatsu, Yusuke
    Harada, Toshiro
    EUROPEAN JOURNAL OF ORGANIC CHEMISTRY, 2010, 2010 (34) : 6535 - 6538
  • [47] CATALYTIC, ENANTIOSELECTIVE DIENOLATE ADDITIONS TO ALDEHYDES - PREPARATION OF OPTICALLY-ACTIVE ACETOACETATE ALDOL ADDUCTS
    SINGER, RA
    CARREIRA, EM
    JOURNAL OF THE AMERICAN CHEMICAL SOCIETY, 1995, 117 (49) : 12360 - 12361
  • [48] Aryl Bromides as Inexpensive Starting Materials in the Catalytic Enantioselective Arylation of Aryl Aldehydes: The Additive TMEDA Enhances the Enantioselectivity
    Yang, Yong-Xin
    Liu, Yue
    Zhang, Lei
    Jia, Yan-E
    Wang, Pei
    Zhuo, Fang-Fang
    An, Xian-Tao
    Da, Chao-Shan
    JOURNAL OF ORGANIC CHEMISTRY, 2014, 79 (21): : 10696 - 10702
  • [49] Activation of functional arylzincs prepared from aryl iodides and highly enantioselective addition to aldehydes
    DeBerardinis, Albert M.
    Turlington, Mark
    Pu, Lin
    ORGANIC LETTERS, 2008, 10 (13) : 2709 - 2712
  • [50] Highly efficient catalytic system for enantioselective Michael addition of aldehydes to nitroalkenes in water
    Zhu, Shaolin
    Yu, Shouyun
    Ma, Dawei
    ANGEWANDTE CHEMIE-INTERNATIONAL EDITION, 2008, 47 (03) : 545 - 548