Chiral Tetraaminophosphonium Carboxylate-Catalyzed Direct Mannich-Type Reaction

被引：178
|
作者：
Uraguchi, Daisuke [1 ]
Ueki, Yusuke [1 ]
Ooi, Takashi [1 ]
机构：
[1] Nagoya Univ, Grad Sch Engn, Dept Appl Chem, Nagoya, Aichi 4648603, Japan
来源：
JOURNAL OF THE AMERICAN CHEMICAL SOCIETY | 2008年 / 130卷 / 43期
关键词：
D O I：
10.1021/ja806311e
中图分类号：
O6 [化学];
学科分类号：
0703 ;
摘要：
The cooperative asymmetric catalysis of chiral tetraaminophosphonium carboxylate (P,S)-1-OCOR has been established, and its synthetic utility has been successfully demonstrated by application to the highly enantioselective direct Mannich-type reaction of azlactones with N-sulfonyl imines. The present study stimulates the cultivation of the potential of the chiral quaternary onium salt catalysis by the structural modification of organic anion.
引用
收藏
页码：14088 / +
页数：3
相关论文
共 50 条
  • [1] Chiral tetraaminophosphonium carboxylate-catalyzed direct mannich-type reaction
    Uraguchi, Daisuke
    Ueki, Yusuke
    Ooi, Takashi
    Journal of the American Chemical Society, 2008, 130 (43): : 14088 - 14089
  • [2] Enantioselective Mannich-type reaction catalyzed by a chiral Bronsted acid
    Akiyama, T
    Itoh, J
    Yokota, K
    Fuchibe, K
    ANGEWANDTE CHEMIE-INTERNATIONAL EDITION, 2004, 43 (12) : 1566 - 1568
  • [3] Chiral bronsted acid catalyzed enantioselective Mannich-type reaction
    Yamanaka, Masahiro
    Itoh, Junji
    Fuchibe, Kohei
    Akiyama, Takahiko
    JOURNAL OF THE AMERICAN CHEMICAL SOCIETY, 2007, 129 (21) : 6756 - 6764
  • [4] Chiral Brønsted acid catalyzed enantioselective Mannich-type reaction
    Department of Chemistry, Faculty of Science, Gakushuin University, 1-5-1 Mejiro, Toshima-ku, Tokyo 171-8588, Japan
    不详
    Journal of the American Chemical Society, 2007, 129 (21): : 6756 - 6764
  • [5] Preparation of β-amino esters by a chiral bronsted acid catalyzed Mannich-type reaction
    Itoh, Junji
    Fuchibe, Kohei
    Akiyama, Takahiko
    SYNTHESIS-STUTTGART, 2008, (08): : 1319 - 1322
  • [6] Chiral ammonium betaine-catalyzed asymmetric Mannich-type reaction of oxindoles
    Torii, Masahiro
    Kato, Kohsuke
    Uraguchi, Daisuke
    Ooi, Takashi
    BEILSTEIN JOURNAL OF ORGANIC CHEMISTRY, 2016, 12 : 2099 - 2103
  • [7] Enantioselective Mannich-type reaction catalyzed by a chiral bronsted acid derived from TADDOL
    Akiyama, T
    Saitoh, Y
    Morita, H
    Fuchibe, K
    ADVANCED SYNTHESIS & CATALYSIS, 2005, 347 (11-13) : 1523 - 1526
  • [8] Vinylogous Mannich-type reaction catalyzed by an iodine-substituted chiral phosphoric acid
    Akiyama, Takahiko
    Honma, Yasuhiro
    Itoh, Junji
    Fuchibe, Kohei
    ADVANCED SYNTHESIS & CATALYSIS, 2008, 350 (03) : 399 - 402
  • [9] Chiral Bronsted Acid-Catalyzed Stereoselective Mannich-Type Reaction of Azlactones with Aldimines
    Avila, Eloah P.
    Justo, Rodrigo M. S.
    Goncalves, Vanessa P.
    Pereira, Adriane A.
    Diniz, Renata
    Amarante, Giovanni W.
    JOURNAL OF ORGANIC CHEMISTRY, 2015, 80 (01): : 590 - 594
  • [10] Asymmetric Mannich-type reaction catalyzed by palladium complexes
    Fujii, A
    Hagiwara, E
    Sodeoka, M
    JOURNAL OF SYNTHETIC ORGANIC CHEMISTRY JAPAN, 2000, 58 (08) : 728 - 735
12345