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
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
  • [41] Enantioselective silylcyanation of aldehydes catalyzed by new chiral oxovanadium complex
    Chu, Chang-Ying
    Hsu, Chu-Tin
    Lo, Po Hsiang
    Uang, Biing-Jiun
    TETRAHEDRON-ASYMMETRY, 2011, 22 (23) : 1981 - 1984
  • [42] Enantioselective diethylzinc additions to aldehydes catalyzed by chiral relay ligands
    Sibi, MP
    Stanley, LM
    TETRAHEDRON-ASYMMETRY, 2004, 15 (21) : 3353 - 3356
  • [43] Highly enantioselective cyanosilylation of aldehydes catalyzed by a chiral oxazaborolidinium ion
    Corey, E.J. (corey@chemistry.harvard.edu), 1600, American Chemical Society, Columbus, United States (126):
  • [44] Axially chiral N,N′-dioxides ethers for catalysis in enantioselective allylation of aldehydes
    Wu, Shijie
    Xing, Yongfei
    Wang, Jie
    Guo, Xingchen
    Zhu, Huajie
    Li, Wan
    CHIRALITY, 2019, 31 (11) : 947 - 957
  • [46] Synthesis of Chiral Axially Diaryl Aldehydes by Chiral Phosphoric Acid Catalyzed Desymmetrization Reaction
    Yuan, Lutong
    Cui, Lixin
    Liu, Yuheng
    Bao, Wenkai
    Zhu, Qiaohong
    Zeng, Xiaofei
    EUROPEAN JOURNAL OF ORGANIC CHEMISTRY, 2025, 28 (02)
  • [47] Enantioselective and Band-Gap Modulation in Photocatalysis of Metal-Free Chiral Carbon Dots
    Zhang, Mengling
    Zhang, Yan
    Du, Xin
    Ma, Yurong
    Huang, Hui
    Liao, Fan
    Fan, Xing
    Wang, Jianhua
    Lin, Haiping
    Shao, Mingwang
    Liu, Yang
    Li, Youyong
    Kang, Zhenhui
    ACS APPLIED MATERIALS & INTERFACES, 2024, 16 (15) : 19379 - 19390
  • [48] Sulfamic Acid-Catalyzed Thioacetalization of Aldehydes under Solvent and Metal-Free Conditions
    Leitemberger, Andrielli
    Bohs, Lucas M. C.
    Peixoto, Maura L. B.
    Rosa, Clarissa H.
    Rosa, Gilber R.
    Godoi, Marcelo
    CHEMISTRYSELECT, 2020, 5 (27): : 8253 - 8257
  • [49] Chiral Phosphoric Acid Catalyzed Asymmetric Synthesis of Axially Chiral Compounds†
    Da, Bing-Chao
    Xiang, Shao-Hua
    Li, Shaoyu
    Tan, Bin
    CHINESE JOURNAL OF CHEMISTRY, 2021, 39 (07) : 1787 - 1796
  • [50] Metal-Free Selective Synthesis of α,β-Unsaturated Aldehydes from Alkenes and Formaldehyde Catalyzed by Dimethylamine
    Peng, Gongming
    Ullah, Naseeb
    Streiff, Stephane
    Vigier, Karine De Oliveira
    Pera-Titus, Marc
    Wischert, Raphael
    Jerome, Francois
    CHEMISTRY-A EUROPEAN JOURNAL, 2024, 30 (29)