Ru-Catalyzed Asymmetric Addition of Arylboronic Acids to Aliphatic Aldehydes via P-Chiral Monophosphorous Ligands

被引：5
|
作者：
Miao, Rui [1 ]
Xia, Yanping [1 ]
Wei, Yifei [1 ]
Ouyang, Lu [1 ]
Luo, Renshi [1 ,2 ]
机构：
[1] Gannan Med Univ, Sch Pharm, Ganzhou 341000, Peoples R China
[2] Shaoguan Univ, Coll Chem & Environm Engn, Shaoguan 512005, Peoples R China
来源：
MOLECULES | 2022年 / 27卷 / 12期
基金：
中国国家自然科学基金;
关键词：
Ru-catalyzed; asymmetric addition; P-chiral monophosphorous ligands; chiral alcohols; TRANSFER HYDROGENATION; SECONDARY ALCOHOLS; ENANTIOSELECTIVE SYNTHESIS; ORGANOBORONIC ACIDS; EFFICIENT SYNTHESIS; CARBONYL-COMPOUNDS; GRIGNARD-REAGENTS; BETA-ALKYLATION; OLEFIN LIGANDS; ARYLATION;
D O I：
10.3390/molecules27123898
中图分类号：
Q5 [生物化学]; Q7 [分子生物学];
学科分类号：
071010 ; 081704 ;
摘要：
Chiral alcohols are among the most widely applied in fine chemicals, pharmaceuticals and agrochemicals. Herein, the Ru-monophosphine catalyst formed in situ was found to promote an enantioselective addition of aliphatic aldehydes with arylboronic acids, delivering the chiral alcohols in excellent yields and enantioselectivities and exhibiting a broad scope of aliphatic aldehydes and arylboronic acids. The enantioselectivities are highly dependent on the monophosphorous ligands. The utility of this asymmetric synthetic method was showcased by a large-scale transformation.
引用
收藏
页数：18
相关论文
共 50 条
  • [11] P-Chiral monodentate diamidophosphites as ligands for Rh-catalyzed asymmetric reactions
    S. E. Lyubimov
    V. A. Davankov
    P. V. Petrovskii
    N. M. Loim
    Russian Chemical Bulletin, 2007, 56 : 2094 - 2096
  • [12] Ru-catalyzed 1,4-addition of arylboronic acids to acrylic acid derivatives in the presence of phenols
    Zhang, Lei
    Xie, Xiaomin
    Peng, Zhiyong
    Fu, Lei
    Zhang, Zhaoguo
    CHEMICAL COMMUNICATIONS, 2013, 49 (78) : 8797 - 8799
  • [13] P-Chiral Monophosphorus Ligands for Asymmetric Copper-Catalyzed Allylic Alkylation
    Xiong, Wenrui
    Xu, Guangqing
    Yu, Xinhong
    Tang, Wenjun
    ORGANOMETALLICS, 2019, 38 (20) : 4003 - 4013
  • [14] P-Chiral monodentate diamidophosphites as ligands for Rh-catalyzed asymmetric reactions
    Lyubimov, S. E.
    Davankov, V. A.
    Petrovskii, P. V.
    Loim, N. M.
    RUSSIAN CHEMICAL BULLETIN, 2007, 56 (10) : 2094 - 2096
  • [15] Chiral olefin-sulfoxide as ligands for rhodium-catalyzed asymmetric conjugate addition of arylboronic acids to unsaturated esters
    Xue, Feng
    Wang, Dongping
    Li, Xincheng
    Wan, Boshun
    ORGANIC & BIOMOLECULAR CHEMISTRY, 2013, 11 (45) : 7893 - 7898
  • [16] P-chiral phosphine ligands for transition-metal-catalyzed asymmetric reactions
    Imamoto, Tsuneo
    JOURNAL OF SYNTHETIC ORGANIC CHEMISTRY JAPAN, 2007, 65 (11) : 1060 - 1069
  • [17] Chiral tetrafluorobenzobarrelenes as highly efficient ligands for the rhodium-catalyzed asymmetric 1,4-addition of arylboronic acids
    Nishimura, Takahiro
    Nagaosa, Makoto
    Hayashi, Tamio
    CHEMISTRY LETTERS, 2008, 37 (08) : 860 - 861
  • [18] ORGN 435-Novel planar chiral imidazolium salts in the asymmetric rhodium-catalyzed addition of arylboronic acids to aldehydes
    Ma, Qingshuang
    Ma, Yudao
    Duan, Wenzeng
    Xia, Houqi
    Song, Chun
    ABSTRACTS OF PAPERS OF THE AMERICAN CHEMICAL SOCIETY, 2008, 236
  • [19] Pd(II)-Catalyzed Asymmetric Addition of Arylboronic Acids to Aliphatic N-Carbamoyl Hydrazones
    Alberca, Saul
    Velazquez, Marta
    Trujillo-Sierra, Jose
    Iglesias-Siguenza, Javier
    Fernandez, Rosario
    Lassaletta, Jose M.
    Monge, David
    ADVANCED SYNTHESIS & CATALYSIS, 2022, 364 (14) : 2373 - 2379
  • [20] Efficient P-Chiral Biaryl Bisphosphorus Ligands for Palladium-Catalyzed Asymmetric Hydrogenation
    Jiang, Wenhao
    Zhao, Qing
    Tang, Wenjun
    CHINESE JOURNAL OF CHEMISTRY, 2018, 36 (02) : 153 - 156
12345