Salen-derived catalysts containing secondary basic groups in the addition of diethylzinc to aldehydes

被引:84
|
作者
DiMauro, EF [1 ]
Kozlowski, MC [1 ]
机构
[1] Univ Penn, Roy & Diana Vagelos Labs, Dept Chem, Philadelphia, PA 19104 USA
关键词
D O I
10.1021/ol016535u
中图分类号
O62 [有机化学];
学科分类号
070303 ; 081704 ;
摘要
[GRAPHICS] A set of modular bifunctional salen catalysts which contain Lewis acid and Lewis base activating groups is described. These groups can be altered independently to control nucleophilic and electrophilic activation of the reacting substrates, These salen-derived catalysts show enhanced reactivity in the addition of diethylzinc to aldehydes with respect to most other salen, amino alcohol, and diamine derived catalysts and reactivity comparable to that of Ti complexes of bis-sulfonamides and diols.
引用
收藏
页码:3053 / 3056
页数:4
相关论文
共 50 条
  • [31] CATALYTIC ENANTIOSELECTIVE ADDITION OF DIETHYLZINC TO ALDEHYDES BY CHIRAL SECONDARY GAMMA-AMINOALCOHOLS
    CHO, BT
    KIM, N
    BULLETIN OF THE KOREAN CHEMICAL SOCIETY, 1994, 15 (11) : 931 - 932
  • [32] Imines derived from (1S,2R)-norephedrine as catalysts in the enantioselective addition of diethylzinc to aldehydes
    Jaworska, Magdalena
    Laczkowski, Krzysztof Z.
    Wekniak, Miroslaw
    Welke, Magdalena
    Wojtczak, Andrzej
    APPLIED CATALYSIS A-GENERAL, 2009, 357 (02) : 150 - 158
  • [33] Synthesis of novel nitrogen-containing ligands for the enantioselective addition of diethylzinc to aldehydes
    Fonseca, MH
    Eibler, E
    Zabel, M
    König, B
    TETRAHEDRON-ASYMMETRY, 2003, 14 (14) : 1989 - 1994
  • [34] Asymmetric addition of diethylzinc to aldehydes catalyzed by a camphor-derived β-amino alcohol
    Wu, Zhi-Long
    Wu, Hsyueh-Liang
    Wu, Ping-Yu
    Uang, Biing-Jiun
    TETRAHEDRON-ASYMMETRY, 2009, 20 (13) : 1556 - 1560
  • [35] L-Alanine-derived Chiral Ligands for Asymmetric Addition of Diethylzinc to Aldehydes
    Kang, Seock Yong
    Baek, Jinho
    Kang, Kyoung Hee
    Lee, Jeong-ae
    Park, Yong Sun
    BULLETIN OF THE KOREAN CHEMICAL SOCIETY, 2012, 33 (09): : 3125 - 3128
  • [36] New chiral ligands derived from (+) and (-)-α-pinene for the enantioselective addition of diethylzinc to aldehydes
    Frensch, Gustavo
    Labes, Ricardo
    Wosch, Celso Luiz
    Munaretto, Laieli dos Santos
    Salome, Kahlil Schwanka
    Guerrero, Palimecio G., Jr.
    Marques, Francisco A.
    TETRAHEDRON LETTERS, 2016, 57 (03) : 420 - 422
  • [37] Enantioselective addition of diethylzinc to aldehydes catalyzed by γ-amino alcohols derived from (+)- and (-)-α-pinene
    Szakonyi, Z
    Balázs, A
    Martinek, TA
    Fülöp, F
    TETRAHEDRON-ASYMMETRY, 2006, 17 (02) : 199 - 204
  • [38] Novel, cyclic and bicyclic 1,3-diols as catalysts for the diethylzinc addition to aldehydes
    Sarvary, I
    Wan, YQ
    Frejd, T
    JOURNAL OF THE CHEMICAL SOCIETY-PERKIN TRANSACTIONS 1, 2002, (05): : 645 - 651
  • [39] Synthesis of new chiral catalysts, 2-azanorbornyloxazolidines, for enantioselective addition of diethylzinc to aldehydes
    Nakano, H
    Okuyama, Y
    Iwasa, K
    Hongo, H
    HETEROCYCLES, 2001, 54 (01) : 411 - 418
  • [40] ENANTIOSELECTIVE ADDITION OF DIETHYLZINC TO ALDEHYDES USING CHIRAL POLYMER CATALYSTS POSSESSING A METHYLENE SPACER
    WATANABE, M
    SOAI, K
    JOURNAL OF THE CHEMICAL SOCIETY-PERKIN TRANSACTIONS 1, 1994, (07): : 837 - 842