Rhodium Catalyzed Asymmetric Hydrogenation of 2-Pyridine Ketones

被引：62
作者：
Yang, Hailong
Huo, Ningning
Yang, Ping
Pei, Hao
Lv, Hui [1 ]
Zhang, Xumu
机构：
[1] Wuhan Univ, Key Lab Biomed Polymers, Minist Educ, Wuhan 430072, Hubei, Peoples R China
来源：
ORGANIC LETTERS | 2015年 / 17卷 / 17期
基金：
中国国家自然科学基金;
关键词：
HIGHLY ENANTIOSELECTIVE HYDROGENATION; IRIDIUM CATALYSTS; KINETIC RESOLUTION; PYRIDYL ALCOHOLS; CU(II)(BORABOX)-CATALYZED ACYLATION; STEREOSELECTIVE HYDROGENATION; ABSOLUTE-CONFIGURATION; HETEROAROMATIC KETONES; EFFICIENT; LIGANDS;
D O I：
10.1021/acs.orglett.5b01878
中图分类号：
O62 [有机化学];
学科分类号：
070303 ; 081704 ;
摘要：
Catalyzed by [Rh(COD)Binapine]BF4, the asymmetric hydrogenation of 2-pyridine ketones has been achieved with excellent enantioselectivities (enantiomeric excesses up to 99%) under mild conditions. This method is suitable for various kinds of 2-pyridine ketones and their derivatives. A number of enantiomerically pure chiral 2-pyridine-aryl/alkyl alcohols were prepared through hydrogenation, which can be used directly in organic synthesis.
引用
收藏
页码：4144 / 4147
页数：4
相关论文
共 50 条
  • [41] Asymmetric transfer hydrogenation of ketones catalyzed by chiral macrocyclic cobalt(II) complexes
    Ruan, Sun-Hong
    Fan, Zi-Wei
    Zhang, Wen-Jing
    Xu, Han
    An, Dong -Li
    Wei, Zan-Bin
    Yuan, Ru-Ming
    Gao, Jing-Xing
    Li, Yan-Yun
    JOURNAL OF CATALYSIS, 2023, 418 : 100 - 109
  • [42] Manganese Catalyzed Asymmetric Transfer Hydrogenation of Ketones Using Chiral Oxamide Ligands
    Schneekoenig, Jacob
    Junge, Kathrin
    Beller, Matthias
    SYNLETT, 2019, 30 (04) : 503 - 507
  • [43] Chiral phosphabarrelene ligands: Synthesis and evaluation in rhodium-catalyzed asymmetric hydrogenation
    Breit, Bernhard
    Fuchs, Evelyn
    SYNTHESIS-STUTTGART, 2006, (13): : 2121 - 2128
  • [44] Aqueous biphasic iron-catalyzed asymmetric transfer hydrogenation of aromatic ketones
    Demmans, K. Z.
    Ko, O. W. K.
    Morris, R. H.
    RSC ADVANCES, 2016, 6 (91): : 88580 - 88587
  • [45] Cobalt-catalyzed asymmetric hydrogenation of ketones: A remarkable additive effect on enantioselectivity
    Du, Tian
    Wang, Biwen
    Wang, Chao
    Xiao, Jianliang
    Tang, Weijun
    CHINESE CHEMICAL LETTERS, 2021, 32 (03) : 1241 - 1244
  • [46] On the NH Effect in Ruthenium-Catalysed Hydrogenation of Ketones: Rational Design of Phosphine-Amino-Alcohol Ligands for Asymmetric Hydrogenation of Ketones
    Phillips, Scott D.
    Fuentes, Jose A.
    Clarke, Matthew L.
    CHEMISTRY-A EUROPEAN JOURNAL, 2010, 16 (27) : 8002 - 8005
  • [47] Synthesis of chiral cyclic β-amino ketones by Ru-catalyzed asymmetric hydrogenation
    Huang, Kexuan
    Guan, Zheng-Hui
    Zhang, Xumu
    TETRAHEDRON LETTERS, 2014, 55 (10) : 1686 - 1688
  • [48] Pd-Catalyzed Asymmetric Hydrogenation of C=C Bond of α,β-Unsaturated Ketones
    Wang, Duo-Sheng
    Wang, Da-Wei
    Zhou, Yong-Gui
    SYNLETT, 2011, (07) : 947 - 950
  • [49] Cycloheptyl-fused-PNN-manganese catalyzed asymmetric transfer hydrogenation of ketones
    Wang, Zechen
    Zhang, Shuo
    Ma, Zhifeng
    Li, Libin
    Yan, Xiuli
    Cao, Qianrong
    Su, Yi
    Ma, Ning
    Wang, Zheng
    MOLECULAR CATALYSIS, 2024, 564
  • [50] Rhodium-Catalyzed Asymmetric Hydrogenation of Tetrasubstituted α,β-Unsaturated Amides: Efficient Access to Chiral β-Amino Amides
    Jiao, Bing
    Wang, Fangyuan
    Lv, Hui
    CHINESE JOURNAL OF CHEMISTRY, 2024, 42 (21) : 2641 - 2646
12345