Rhodium-catalyzed asymmetric hydrogenation of unprotected β-enamine phosphonates

被引:11
|
作者
Zhou, Ming [1 ]
Xue, Zejian [1 ]
Cao, Min [1 ]
Dong, Xiu-Qin [1 ]
Zhang, Xumu [1 ]
机构
[1] Wuhan Univ, Coll Chem & Mol Sci, Wuhan 430072, Hubei, Peoples R China
基金
中国国家自然科学基金;
关键词
ALPHA-AMINO; AMINOPHOSPHONATES; INHIBITOR;
D O I
10.1039/c6ob00540c
中图分类号
O62 [有机化学];
学科分类号
070303 ; 081704 ;
摘要
We have successfully developed a strategy for the first time for the enantioselective Rh-TaniaPhos catalyzed asymmetric hydrogenation of unprotected beta-enamine phosphonates to free beta-amino phosphonates directly with good enantioselectivities (80%-86% ee) and high conversions (>99% conversion). The resulting chiral free beta-amino phosphonates and their derivatives are important intermediates in biochemistry and pharmaceuticals.
引用
收藏
页码:4582 / 4584
页数:3
相关论文
共 50 条
  • [1] Rhodium-Catalyzed Asymmetric Hydrogenation of Unprotected NH Imines Assisted by a Thiourea
    Zhao, Qingyang
    Wen, Jialin
    Tan, Renchang
    Huang, Kexuan
    Metola, Pedro
    Wang, Rui
    Anslyn, Eric V.
    Zhang, Xumu
    ANGEWANDTE CHEMIE-INTERNATIONAL EDITION, 2014, 53 (32) : 8467 - 8470
  • [2] Rhodium-Catalyzed Highly Enantioselective Hydrogenation of a Tetrasubstituted Enamine
    Yamada, Masatoshi
    Kato, Tomoaki
    Ikemoto, Tomomi
    Yamano, Mitsuhisa
    ORGANIC PROCESS RESEARCH & DEVELOPMENT, 2021, 25 (04) : 1074 - 1079
  • [3] Rhodium-catalyzed asymmetric hydrogenation of β-acetylamino acrylonitriles
    Ma, Miaofeng
    Hou, Guohua
    Wang, Junru
    Zhang, Xumu
    TETRAHEDRON-ASYMMETRY, 2011, 22 (05) : 506 - 511
  • [4] Rhodium-Catalyzed Enantioselective Hydrogenation of Unsaturated Phosphonates by ClickFerrophos Ligands
    Konno, Takashi
    Shimizu, Kenta
    Ogata, Kenichi
    Fukuzawa, Shin-ichi
    JOURNAL OF ORGANIC CHEMISTRY, 2012, 77 (07): : 3318 - 3324
  • [5] Rhodium-Catalyzed Asymmetric Hydrogenation and Transfer Hydrogenation of α-Nitro Ketones
    Sun, Hao
    Xu, Liren
    Ruan, Sai
    Ratovelomanana-Vidal, Virginie
    Chen, Gen-Qiang
    Zhang, Xumu
    ORGANIC LETTERS, 2024, 26 (46) : 10008 - 10012
  • [6] Attraction versus Repulsion in Rhodium-Catalyzed Asymmetric Hydrogenation
    Gridnev, Ilya D.
    CHEMCATCHEM, 2016, 8 (22) : 3463 - 3465
  • [7] Rhodium-Catalyzed Homogeneous Asymmetric Hydrogenation of Naphthol Derivatives
    Zhang, Shu-Xin
    Long, Linhong
    Li, Zeyu
    He, Yan-Mei
    Li, Shan
    Chen, Hui
    Hao, Wei
    Fan, Qing-Hua
    JOURNAL OF THE AMERICAN CHEMICAL SOCIETY, 2025, 147 (06) : 5197 - 5211
  • [8] MECHANISTIC STUDIES OF RHODIUM-CATALYZED ASYMMETRIC HOMOGENEOUS HYDROGENATION
    BROWN, JM
    CHALONER, PA
    PARKER, D
    ADVANCES IN CHEMISTRY SERIES, 1982, (196): : 355 - 369
  • [9] Highly Efficient Iridium-Catalyzed Asymmetric Hydrogenation of Unprotected β-Enamine Esters
    Hou, Guohua
    Li, Wei
    Ma, Miaofeng
    Zhang, Xiaowei
    Zhang, Xumu
    JOURNAL OF THE AMERICAN CHEMICAL SOCIETY, 2010, 132 (37) : 12844 - 12846
  • [10] Rhodium-catalyzed asymmetric hydrogenation of exocyclic α,β-unsaturated carbonyl compounds
    Yang, Jiaxin
    Li, Xiuxiu
    You, Cai
    Li, Shuailong
    Guan, Yu-Qing
    Lv, Hui
    Zhang, Xumu
    ORGANIC & BIOMOLECULAR CHEMISTRY, 2020, 18 (05) : 856 - 859