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
  • [1] The first highly enantioselective catalytic diphenylzinc additions to aldehydes: Synthesis of chiral diarylcarbinols by asymmetric catalysis
    Huang, WS
    Pu, L
    JOURNAL OF ORGANIC CHEMISTRY, 1999, 64 (12): : 4222 - 4223
  • [2] First highly enantioselective catalytic diphenylzinc additions to aldehydes: Synthesis of chiral diarylcarbinols by asymmetric catalysis
    Huang, Wei-Sheng
    Pu, Lin
    Journal of Organic Chemistry, 1999, 64 (12):
  • [3] Catalytic enantioselective aryl transfer:: asymmetric addition of diphenylzinc to aldehydes
    Bolm, C
    Muñiz, K
    CHEMICAL COMMUNICATIONS, 1999, (14) : 1295 - 1296
  • [4] Enantioselective additions of diphenylzinc to aldehydes using chiral pyrrolidinylmethanol derivatives as catalysts
    Zhao, G
    Li, XG
    Wang, XR
    TETRAHEDRON-ASYMMETRY, 2001, 12 (03) : 399 - 403
  • [5] Catalytic enantioselective arylation of aryl aldehydes by chiral aminophenol ligands
    Yang, Xiao-Feng
    Hirose, Takuji
    Zhang, Guang-You
    TETRAHEDRON-ASYMMETRY, 2009, 20 (04) : 415 - 419
  • [6] Chiral Chalcogen Peptides as Ligands for the Catalytic Enantioselective Aryl Transfer Reaction to Aldehydes
    Schwab, Ricardo S.
    Soares, Letiere C.
    Dornelles, Luciano
    Rodrigues, Oscar E. D.
    Paixao, Marcio W.
    Godoi, Marcelo
    Braga, Antonio L.
    EUROPEAN JOURNAL OF ORGANIC CHEMISTRY, 2010, 2010 (19) : 3574 - 3578
  • [7] Structural optimization of enantiopure 2-cyclialkylamino-2-aryl-1,1-diphenylethanols as catalytic ligands for enantioselective additions to aldehydes
    Rodriguez-Escrich, Sergi
    Reddy, Katamreddy Subba
    Jimeno, Ciril
    Colet, Gisela
    Rodriguez-Escrich, Carles
    Sola, Lluis
    Vidal-Ferran, Anton
    Pericas, Miquel A.
    JOURNAL OF ORGANIC CHEMISTRY, 2008, 73 (14): : 5340 - 5353
  • [8] Highly effective and recyclable dendritic ligands for the enantioselective aryl transfer reactions to aldehydes
    Liu, XY
    Wu, XY
    Chai, Z
    Wu, YY
    Zhao, G
    Zhu, SZ
    JOURNAL OF ORGANIC CHEMISTRY, 2005, 70 (18): : 7432 - 7435
  • [9] Catalytic enantioselective aryl transfer to aldehydes.
    Bolm, C
    Muniz, K
    Hildebrand, JP
    Hermanns, N
    Kesselgruber, M
    Rudolph, J
    ABSTRACTS OF PAPERS OF THE AMERICAN CHEMICAL SOCIETY, 2001, 221 : U174 - U174
  • [10] Catalytic enantioselective aldol additions of α-isothiocyanato imides to aldehydes
    Li, Le
    Klauber, Eric G.
    Seidel, Daniel
    JOURNAL OF THE AMERICAN CHEMICAL SOCIETY, 2008, 130 (37) : 12248 - +