Synthesis of enantiopure β2-homoalanine derivatives via rhodium catalyzed asymmetric hydrogenation

被引：5
作者：
Luehr, Susan [1 ]
Holz, Jens [1 ]
Zayas, Odalys [2 ]
Seidelmann, Oliver [3 ]
Domke, Lutz [1 ]
Boerner, Armin [1 ,2 ]
机构：
[1] Univ Rostock eV, Leibniz Inst Katalyse, D-18059 Rostock, Germany
[2] Univ Rostock, Inst Chem, D-18059 Rostock, Germany
[3] ChiroBlock GmbH, D-06766 Wolfen, Germany
来源：
TETRAHEDRON-ASYMMETRY | 2013年 / 24卷 / 07期
关键词：
BETA-AMINO ACIDS; R-SMS-PHOS; ENANTIOSELECTIVE SYNTHESIS; BETA(2)-AMINO ACIDS; STEREOSELECTIVE HYDROGENATION; KINETIC RESOLUTION; LIGANDS; ACRYLATES; CYCLAMENOL; ADDITIONS;
D O I：
10.1016/j.tetasy.2013.02.011
中图分类号：
O61 [无机化学];
学科分类号：
070301 ; 081704 ;
摘要：
The stereoselective synthesis of chiral beta(2)-homoalanine derivatives with 99% ee by the Rh-catalyzed enantioselective hydrogenation of prochiral 2-aminomethyl acrylates is described. The subsequent transformation to chiral 3-amino-2-methylpropanols is also demonstrated. (c) 2013 Elsevier Ltd. All rights reserved.
引用
收藏
页码：395 / 401
页数：7
相关论文
共 50 条
  • [1] Rhodium Catalyzed Asymmetric Hydrogenation of 2-Pyridine Ketones
    Yang, Hailong
    Huo, Ningning
    Yang, Ping
    Pei, Hao
    Lv, Hui
    Zhang, Xumu
    ORGANIC LETTERS, 2015, 17 (17) : 4144 - 4147
  • [2] Synthesis of Enantiopure γ-Lactones via a RuPHOX-Ru Catalyzed Asymmetric Hydrogenation of γ-Keto Acids
    Li, Jing
    Ma, Yujie
    Lu, Yufei
    Liu, Yangang
    Liu, Delong
    Zhang, Wanbin
    ADVANCED SYNTHESIS & CATALYSIS, 2019, 361 (05) : 1146 - 1153
  • [3] Synthesis of Chiral β-Amino Nitroalkanes via Rhodium-Catalyzed Asymmetric Hydrogenation
    Li, Pan
    Zhou, Ming
    Zhao, Qingyang
    Wu, Weilong
    Hu, Xinquan
    Dong, Xiu-Qin
    Zhang, Xumu
    ORGANIC LETTERS, 2016, 18 (01) : 40 - 43
  • [4] 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
  • [5] Rhodium catalyzed asymmetric synthesis of Chiraphos derivatives
    Sun, Ying-Ying
    Zhang, Bin
    Yu, Liangbin
    Cui, Ranran
    Zhao, Qingyang
    Zhang, Qing-Wei
    CHINESE CHEMICAL LETTERS, 2022, 33 (12) : 5084 - 5087
  • [6] Enantioselective Synthesis of Chiral β2-Amino Phosphorus Derivatives via Nickel-Catalyzed Asymmetric Hydrogenation
    Wei, Hanlin
    Luo, Yicong
    Li, Jinhui
    Chen, Jianzhong
    Gridnev, Ilya D.
    Zhang, Wanbin
    JOURNAL OF THE AMERICAN CHEMICAL SOCIETY, 2024, 147 (01) : 342 - 352
  • [7] Rhodium-Catalyzed Asymmetric Synthesis of Spirosilabifluorene Derivatives
    Kuninobu, Yoichiro
    Yamauchi, Kanae
    Tamura, Naoya
    Seiki, Takayuki
    Takai, Kazuhiko
    ANGEWANDTE CHEMIE-INTERNATIONAL EDITION, 2013, 52 (05) : 1520 - 1522
  • [8] Asymmetric synthesis of 2-alkyl-3-phosphonopropanoic acid derivatives via Rh-catalyzed asymmetric hydrogenation
    Luo, Li-Bin
    Wang, Dao-Yong
    Zhou, Xiao-Mao
    Zheng, Zhuo
    Hu, Xiang-Ping
    TETRAHEDRON-ASYMMETRY, 2011, 22 (24) : 2117 - 2123
  • [9] Rhodium-Catalyzed Asymmetric Hydrogenation of Tetrasubstituted Cyclic Enamides: Efficient Access to Chiral Cycloalkylamine Derivatives
    Li, Xiuxiu
    You, Cai
    Yang, Hailong
    Che, Jinteng
    Chen, Pengyu
    Yang, Yusheng
    Lv, Hui
    Zhang, Xumu
    ADVANCED SYNTHESIS & CATALYSIS, 2017, 359 (04) : 597 - 602
  • [10] Synthesis and Resolution of 3,3′-Disubstituted xylBINAP Derivatives and Their Application in Rhodium-Catalyzed Asymmetric Hydrogenation
    Rankic, Danica A.
    Hopkins, J. Matthew
    Parvez, Masood
    Keay, Brian A.
    SYNLETT, 2009, (15) : 2513 - 2517
12345