The first asymmetric synthesis of trialkyl phosphates on the basis of dynamic kinetic resolution in the phosphite method using a chiral source in a catalytic manner

被引:15
|
作者
Hayakawa, Y [1 ]
Hyodo, M [1 ]
Kimura, K [1 ]
Kataoka, M [1 ]
机构
[1] Nagoya Univ, Grad Sch Human Informat, Bioorgan Chem Lab, Chikusa Ku, Nagoya, Aichi 4648601, Japan
关键词
D O I
10.1039/b304163h
中图分类号
O6 [化学];
学科分类号
0703 ;
摘要
The first asymmetric synthesis of trialkyl phosphates having stereogenic phosphorus atoms on the basis of dynamic kinetic resolution using a chiral source in a catalytic manner; achieved through the stereospecific oxidation of a trialkyl phosphite enantioselectively obtained by the condensation of a racemic unsymmetrically substituted dialkyl phosphorochloridite and an alcohol using a chiral amine as a catalytic promoter.
引用
收藏
页码:1704 / 1705
页数:2
相关论文
共 45 条
  • [21] Catalytic asymmetric aza Diels-Alder reactions using a chiral lanthanide Lewis acid. Enantioselective synthesis of tetrahydroquinoline derivatives using a catalytic amount of a chiral source
    Ishitani, H
    Kobayashi, S
    TETRAHEDRON LETTERS, 1996, 37 (41) : 7357 - 7360
  • [22] Synthesis of Chiral Dihydrobenzofurans and Phthalides by Asymmetric Transfer Hydrogenation via Dynamic Kinetic Resolution: A Strategy for Total Synthesis of Daldinins A, B, and C and Concentricolide
    Fang, Lizhen
    Lyu, Qinghua
    Lu, Chenjuan
    Li, Huanhuan
    Liu, Saisai
    Han, Lili
    ADVANCED SYNTHESIS & CATALYSIS, 2016, 358 (20) : 3196 - 3200
  • [23] Asymmetric Synthesis of Chiral Acyclic Purine Nucleosides Containing a Hemiaminal Ester Moiety via Three-Component Dynamic Kinetic Resolution
    Xie, Ming-Sheng
    Chen, Yang-Guang
    Wu, Xiao-Xia
    Qu, Gui-Rong
    Guo, Hai-Ming
    ORGANIC LETTERS, 2018, 20 (04) : 1212 - 1215
  • [24] Synthesis of Axially Chiral Biaryls through Sulfoxide-Directed Asymmetric Mild C-H Activation and Dynamic Kinetic Resolution
    Hazra, Chinmoy Kumar
    Dherbassy, Quentin
    Wencel-Delord, Joanna
    Colobert, Francoise
    ANGEWANDTE CHEMIE-INTERNATIONAL EDITION, 2014, 53 (50) : 13871 - 13875
  • [25] Concise Synthesis of Chiral Tricyclic Lactams by Tandem Dynamic Kinetic Asymmetric Reductive Amination/Lactamization Using Ammonium Salts
    Wang, Jingxin
    Shi, Yongjie
    Wang, Fangyuan
    Huang, Fanping
    Bai, Shao-Tao
    Zhao, Yu
    Zhang, Xumu
    ANGEWANDTE CHEMIE-INTERNATIONAL EDITION, 2023, 62 (25)
  • [26] First catalytic enantioselective synthesis of P-stereogenic phosphoramides via kinetic resolution promoted by a chiral bicyclic imidazole nucleophilic catalyst
    Liu, Shan
    Zhang, Zhenfeng
    Xie, Fang
    Butt, Nicholas A.
    Sun, Li
    Zhang, Wanbin
    TETRAHEDRON-ASYMMETRY, 2012, 23 (05) : 329 - 332
  • [27] Dynamic kinetic resolution catalyzed by Ir axially chiral phosphine catalyst:: Asymmetric synthesis of anti aromatic β-hydroxy-α-amino acid esters
    Makino, K
    Hiroki, Y
    Hamada, Y
    JOURNAL OF THE AMERICAN CHEMICAL SOCIETY, 2005, 127 (16) : 5784 - 5785
  • [29] Catalytic asymmetric synthesis of axially chiral 2-amino-1,1′-biaryl compounds by phase-transfer-catalyzed kinetic resolution and desymmetrization
    Shirakawa, Seiji
    Wu, Xiangfei
    Liu, Shiyao
    Maruoka, Keiji
    TETRAHEDRON, 2016, 72 (34) : 5163 - 5171
  • [30] Synthesis of Chiral 2-Aroyl-1-tetralols: Asymmetric Transfer Hydrgenation of 2-Aroyl-1-tetralones via Dynamic Kinetic Resolution
    Wu Yun
    Geng Zhicong
    Bai Jinjin
    Zhang Yawen
    CHINESE JOURNAL OF CHEMISTRY, 2011, 29 (07) : 1467 - 1472