Metal-Free Enantioselective Hydroxyamination of Aldehydes with Nitrosocarbonyl Compounds Catalyzed by an Axially Chiral Amine

被引：61
|
作者：
Kano, Taichi [1 ]
Shirozu, Fumitaka [1 ]
Maruoka, Keiji [1 ]
机构：
[1] Kyoto Univ, Dept Chem, Grad Sch Sci, Sakyo Ku, Kyoto 6068502, Japan
来源：
JOURNAL OF THE AMERICAN CHEMICAL SOCIETY | 2013年 / 135卷 / 48期
基金：
日本学术振兴会;
关键词：
ASYMMETRIC ALPHA-AMINOXYLATION; NITROSO ALDOL REACTION; DIELS-ALDER REACTION; AEROBIC OXIDATION; HYDROXAMIC ACIDS; OXYAMINATION; EFFICIENT; CHEMISTRY; ENAMINE; FACILE;
D O I：
10.1021/ja4099627
中图分类号：
O6 [化学];
学科分类号：
0703 ;
摘要：
The first example of a highly regio- and enantioselective hydroxyamination of aldehydes with in situ generated nitrosocarbonyl compounds from hydroxamic acid derivatives was realized by combined use of TEMPO and BPO as the oxidant in the presence of a binaphthyl-modified amine catalyst.
引用
收藏
页码：18036 / 18039
页数：4
相关论文
共 50 条
  • [11] Proline-Tetrazole-Catalyzed Enantioselective N-Nitroso Aldol Reaction of Aldehydes with In Situ Generated Nitrosocarbonyl Compounds
    Maji, Biplab
    Yamamoto, Hisashi
    ANGEWANDTE CHEMIE-INTERNATIONAL EDITION, 2014, 53 (33) : 8714 - 8717
  • [12] Enantioselective Synthesis of Axially Chiral Compounds by Organocatalysts
    Asano, Keisuke
    JOURNAL OF SYNTHETIC ORGANIC CHEMISTRY JAPAN, 2014, 72 (02) : 185 - 186
  • [13] Chiral Phosphoric Acid-Catalyzed Enantioselective Synthesis of Axially Chiral Compounds Involving Indole Derivatives
    Cheng, Jun Kee
    Tan, Bin
    CHEMICAL RECORD, 2023, 23 (11):
  • [14] Transition-Metal-Catalyzed Construction of Axially Chiral Carbonyl Compounds
    Yan, Yu
    Pan, Min
    Ming, Jialin
    Yue, Jun-Ping
    Chen, Xiao-Wang
    Gui, Yong-Yuan
    Yu, Da-Gang
    EUROPEAN JOURNAL OF ORGANIC CHEMISTRY, 2024, 27 (48)
  • [15] Development of Axially Chiral Pyridylidene Amine Ligands and their Application in Pd-Catalyzed Enantioselective Allylic Substitution
    Chen, Zhikang
    Liu, Jiahao
    Ou, Weiying
    Kato, Terumasa
    Wang, Zhe
    Chen, Yong
    Liu, Yan
    Maruoka, Keiji
    JOURNAL OF ORGANIC CHEMISTRY, 2024, 89 (17): : 12800 - 12811
  • [16] Enantioselective addition of diethylzinc to aldehydes catalyzed by chiral hydroxymethylthiazolidines
    Kim, SH
    Chung, ST
    Jin, MJ
    JOURNAL OF INDUSTRIAL AND ENGINEERING CHEMISTRY, 1998, 4 (04) : 345 - 347
  • [17] ENANTIOSELECTIVE ALKYLATION OF ALDEHYDES CATALYZED BY NEW CHIRAL DISELENIDES
    WIRTH, T
    TETRAHEDRON LETTERS, 1995, 36 (43) : 7849 - 7852
  • [18] Phosphoric Acid-Catalyzed Enantioselective Synthesis of Axially Chiral Anthrone-based Compounds
    He, Shi-Jiang
    Zhu, Shuai
    Qiu, Sheng-Qi
    Ding, Wei-Yi
    Cheng, Jun Kee
    Xiang, Shao-Hua
    Tan, Bin
    ANGEWANDTE CHEMIE-INTERNATIONAL EDITION, 2023, 62 (01)
  • [19] Enantioselective trimethylsilylcyanation of aldehydes catalyzed by chiral lanthanoid alkoxides
    Qian, CT
    Zhu, CJ
    Huang, TS
    JOURNAL OF THE CHEMICAL SOCIETY-PERKIN TRANSACTIONS 1, 1998, (14): : 2131 - 2132
  • [20] Chiral Bronsted acid catalyzed enantioselective allenylation of aldehydes
    Reddy, Leleti Rajender
    CHEMICAL COMMUNICATIONS, 2012, 48 (73) : 9189 - 9191
12345