A novel catalytic system for the Mannich-type reaction of silyl enolates:: Stereoselective synthesis of β-aminoketones

被引:0
|
作者
Miura, K
Tamaki, K
Nakagawa, T
Hosomi, A [1 ]
机构
[1] Univ Tsukuba, Dept Chem, Tsukuba, Ibaraki 3058571, Japan
[2] Univ Tsukuba, Grad Sch Chem, Tsukuba, Ibaraki 3058571, Japan
关键词
D O I
10.1002/1521-3773(20000602)39:11<1958::AID-ANIE1958>3.0.CO;2-4
中图分类号
O6 [化学];
学科分类号
0703 ;
摘要
Water and a catalytic amount of iPr2NH effectively induces the Mannich- type reaction of ketone dimethylsilyl enolates with aromatic and α,β- unsaturated N-sulfonylimines, to afford β-aminoketones in good to excellent yields with high levels of anti selectivity [Eq. (1)].
引用
收藏
页码:1958 / +
页数:4
相关论文
共 50 条
  • [1] A novel catalytic system for the Mannich-type reaction of silyl enolates: Stereoselective synthesis of β-aminoketones
    Miura, Katsukiyo
    Tamaki, Kentaro
    Nakagawa, Takahiro
    Hosomi, Akira
    Angewandte Chemie (International Edition in English), 2000, 39 (11): : 1958 - 1960
  • [2] The first catalytic Mannich-type reaction of N-alkoxycarbonylamino sulfones with silyl enolates
    Ollevier, Thierry
    Nadeau, Etienne
    Eguillon, Jean-Christophe
    ADVANCED SYNTHESIS & CATALYSIS, 2006, 348 (15) : 2080 - 2084
  • [3] Stereoselective Mannich-type reaction of chlorotitanium α-phenylseleno esters enolates with aromatic aldimines
    Silveira, CC
    Vieira, AS
    Braga, AL
    Russowsky, D
    TETRAHEDRON, 2005, 61 (39) : 9312 - 9318
  • [4] Catalytic Mannich-type reaction of phosphorylimidates
    Kobayashi, Shu
    Nakano, Junya
    Matsubara, Ryosuke
    TETRAHEDRON, 2010, 66 (33) : 6457 - 6461
  • [5] α-Halo Amides as Competent Latent Enolates: Direct Catalytic Asymmetric Mannich-Type Reaction
    Kumagai, Naoya (nkumagai@bikaken.or.jp), 1600, American Chemical Society (139):
  • [6] α-Halo Amides as Competent Latent Enolates: Direct Catalytic Asymmetric Mannich-Type Reaction
    Sun, Bo
    Balaji, Pandur Venkatesan
    Kumagai, Naoya
    Shibasakia, Masakatsu
    JOURNAL OF THE AMERICAN CHEMICAL SOCIETY, 2017, 139 (24) : 8295 - 8301
  • [7] A novel Mannich-type reaction: lanthanide triflate-catalyzed reactions of N-(a-aminoalkyl)benzotriazoles with silyl enolates
    Kobayashi, S.
    Ishitani, H.
    Komiyama, S.
    Oniciu, D. C.
    Tetrahedron Letters, 37 (21):
  • [8] A novel Mannich-type reaction: Lanthanide triflate-catalyzed reactions of N-(alpha-aminoalkyl)benzotriazoles with silyl enolates
    Kobayashi, S
    Ishitani, H
    Komiyama, S
    Oniciu, DC
    Katritzky, AR
    TETRAHEDRON LETTERS, 1996, 37 (21) : 3731 - 3734
  • [9] Catalytic Asymmetric Mannich-Type Reaction of α-Haloacetonitriles
    Saito, Akira
    Shibasaki, Masakatsu
    ORGANIC LETTERS, 2024, 26 (36) : 7546 - 7550
  • [10] Stereoselective synthesis of δ-amino-α,β,γ,δ-unsaturated cycloketones via Mannich-type reaction
    He, Long
    Qin, Xue
    Qin, Xiao-Yan
    He, Chun-Lan
    Wang, Shi-Da
    Hao, Wen-Juan
    Jiang, Bo
    TETRAHEDRON LETTERS, 2020, 61 (17)