Stereoselective Addition of Diethylzinc to Aldehydes Using Chiral β-Hydroxy-2-oxazolines as Catalysts

被引：2
作者：
Marques, Francisco A. [1 ]
Wosch, Celso L. [1 ]
Frensch, Gustavo [1 ]
Labes, Ricardo [1 ]
Maia, Beatriz H. L. N. S. [1 ]
Salome, Kahlil S. [1 ]
Barison, Andersson [1 ]
Guerrero, Palimecio G., Jr. [2 ]
机构：
[1] Univ Fed Parana, Dept Quim, BR-81531990 Curitiba, PR, Brazil
[2] Univ Tecnol Fed Parana, Dept Quim & Biol, Curitiba, PR, Brazil
来源：
JOURNAL OF THE BRAZILIAN CHEMICAL SOCIETY | 2015年 / 26卷 / 01期
关键词：
(-)-menthone; chiral beta-hydroxy-2-oxazolines; catalysts; diethylzinc; aldehydes; ASYMMETRIC ORGANOZINC ADDITIONS; BINOL-TI COMPLEX; ENANTIOSELECTIVE ADDITION; AMINO-ALCOHOLS; GAMMA-AMINOALCOHOLS; BETA-AMINO; DIALKYLZINC ADDITIONS; AROMATIC-ALDEHYDES; LIGANDS; REAGENTS;
D O I：
10.5935/0103-5053.20140233
中图分类号：
O6 [化学];
学科分类号：
0703 ;
摘要：
Chiral beta-hydroxy-2-oxazolines were synthesized and evaluated as catalysts for the addition of diethylzinc to aldehydes. All oxazolines proved effective in obtaining the addition products. The best enantiomeric excesses (69-78%) were obtained using the chiral beta-hydroxy oxazoline derived from (-)-menthone and the amino alcohol 2-amino-2-methylpropan-1-ol.
引用
收藏
页码：165 / 170
页数：6
相关论文
共 75 条
  • [1] A new, modular approach towards 2-(1-hydroxyalkyl)oxazolines, effective bidentate chiral ligands
    Bauer, Michael
    Kazmaier, Uli
    [J]. JOURNAL OF ORGANOMETALLIC CHEMISTRY, 2006, 691 (10) : 2155 - 2158
  • [2] The Syntheses of new Camphorsulfonylated Ligands Derived from 2-Amino-2'-Hydroxy-1,1'-Binaphthyl and Their Enantioselectivities in the Addition of Dialkylzinc Reagents to Aldehydes
    Bian, Guangling
    Huang, Huayin
    Zong, Hua
    Song, Ling
    [J]. CHIRALITY, 2012, 24 (10) : 825 - 832
  • [3] New chiral ligands derived from mandelic acid: Synthesis and application in the asymmetric phenyl transfer reaction to an aromatic aldehyde
    Bolm, C
    Zani, L
    Rudolph, J
    Schiffers, I
    [J]. SYNTHESIS-STUTTGART, 2004, (13): : 2173 - 2180
  • [4] Acceleration of arylzinc formation and its enantioselective addition to aldehydes by microwave irradiation and aziridine-2-methanol catalysts
    Braga, Antonio L.
    Paixao, Marcio W.
    Westermann, Bernhard
    Schneider, Paulo H.
    Wessjohann, Ludger A.
    [J]. JOURNAL OF ORGANIC CHEMISTRY, 2008, 73 (07) : 2879 - 2882
  • [5] Efficient chirality switching in the addition of diethylzinc to aldehydes in the presence of simple chiral α-amino amides
    Burguete, M. Isabel
    Collado, Manuel
    Escorihuela, Jorge
    Luis, Santiago V.
    [J]. ANGEWANDTE CHEMIE-INTERNATIONAL EDITION, 2007, 46 (47) : 9002 - 9005
  • [6] Bis(ethylsulfonamide)amines via nucleophilic ring-opening of chiral aziridines. Application to Ti-mediated addition of diethylzinc to benzaldehyde
    Cernerud, M
    Skrinning, A
    Bergere, I
    Moberg, C
    [J]. TETRAHEDRON-ASYMMETRY, 1997, 8 (20) : 3437 - 3441
  • [7] Synthesis and application in asymmetric catalysis of camphor-based pyridine ligands
    Chelucci, Giorgio
    [J]. CHEMICAL SOCIETY REVIEWS, 2006, 35 (12) : 1230 - 1243
  • [8] Alternative synthetic route to chiral N-substituted camphor-derived β-amino alcohols
    Cheng, Gin-Ian
    Shei, Chun-Tin
    Sung, Kuangsen
    [J]. CHIRALITY, 2007, 19 (03) : 235 - 238
  • [9] Synthesis of new enantiopure gamma-aminoalcohols: Their use as catalysts in the alkylation of benzaldehyde by diethylzinc
    Cicchi, S
    Crea, S
    Goti, A
    Brandi, A
    [J]. TETRAHEDRON-ASYMMETRY, 1997, 8 (02) : 293 - 301
  • [10] CHIRAL LIGANDS CONTAINING HETEROATOMS .10. 1-(2-PYRIDYL)ALKYLAMINES AS CHIRAL CATALYSTS IN THE ADDITION OF DIETHYLZINC TO ALDEHYDES - TEMPERATURE-DEPENDENCE ON THE ENANTIOSELECTIVITY
    CONTI, S
    FALORNI, M
    GIACOMELLI, G
    SOCCOLINI, F
    [J]. TETRAHEDRON, 1992, 48 (41) : 8993 - 9000
12345678