Highly efficient dynamic kinetic resolution of secondary aromatic alcohols with low-cost and easily available acid resins as racemization catalysts

被引:17
|
作者
Cheng, Yongmei [1 ]
Xu, Gang [1 ]
Wu, Jianping [1 ]
Zhang, Chensheng [1 ]
Yang, Lirong [1 ]
机构
[1] Zhejiang Univ, Inst Bioengn, Dept Biol & Chem Engn, Hangzhou 310027, Zhejiang, Peoples R China
基金
中国国家自然科学基金;
关键词
ENZYMATIC RESOLUTION; RUTHENIUM;
D O I
10.1016/j.tetlet.2010.02.152
中图分类号
O62 [有机化学];
学科分类号
070303 ; 081704 ;
摘要
A new and efficient dynamic kinetic resolution (DKR) process of secondary aromatic alcohols was developed with acid resins as racemization catalysts. Acid resin CD8604 was shown to have excellent racemization activity and good biocompatibility. When employing CD8604 and complex acyl donors as racemization catalyst and acyl donor, respectively, enantiomerically pure aromatic acetate was obtained with excellent yield and ee values through the DKR process. It is noteworthy that the system could be reused more than 10 times with little loss of yield and ee value. (C) 2010 Elsevier Ltd. All rights reserved.
引用
收藏
页码:2366 / 2369
页数:4
相关论文
共 50 条
  • [21] Dynamic kinetic resolution of aromatic sec-alcohols by using a heterogeneous palladium racemization catalyst and lipase
    Xu, Yuanfeng
    Wang, Meng
    Feng, Bo
    Li, Ziyang
    Li, Yuanhua
    Li, Hexing
    Li, Hui
    CATALYSIS SCIENCE & TECHNOLOGY, 2017, 7 (04) : 5838 - 5842
  • [22] Acid zeolites as alcohol racemization catalysts: Screening and application in biphasic dynamic kinetic resolution
    Wuyts, S
    De Temmerman, K
    De Vos, DE
    Jacobs, PA
    CHEMISTRY-A EUROPEAN JOURNAL, 2005, 11 (01) : 386 - 397
  • [23] Efficient dynamic kinetic resolution of secondary alcohols with a novel tetrafluorosuccinato ruthenium complex
    van Nispen, Sjoerd F. G. M.
    van Buijtenen, Jeroen
    Vekemans, Jef A. J. M.
    Meuldijk, Jan
    Hulshof, Lumbertus A.
    TETRAHEDRON-ASYMMETRY, 2006, 17 (15) : 2299 - 2305
  • [24] Readily Available Ruthenium Complex for Efficient Dynamic Kinetic Resolution of Aromatic α-Hydroxy Ketones
    Agrawal, Santosh
    Martinez-Castro, Elisa
    Marcos, Rocio
    Martin-Matute, Belen
    ORGANIC LETTERS, 2014, 16 (08) : 2256 - 2259
  • [25] Dynamic kinetic resolution of secondary alcohols combining enzyme-catalyzed transesterification and zeolite-catalyzed racemization
    Zhu, Yongzhong
    Fow, Kam-Loon
    Chuah, Gaik-Khuan
    Jaenicke, Stephan
    CHEMISTRY-A EUROPEAN JOURNAL, 2007, 13 (02) : 541 - 547
  • [27] (S)-Selective dynamic kinetic resolution of secondary alcohols by the combination of subtilisin and an aminocyclopentadienylruthenium complex as the catalysts
    Kim, MJ
    Chung, YI
    Choi, YK
    Lee, HK
    Kim, D
    Park, J
    JOURNAL OF THE AMERICAN CHEMICAL SOCIETY, 2003, 125 (38) : 11494 - 11495
  • [28] Chemoenzymatic Dynamic Kinetic Resolution of Secondary Alcohols Using an Air- and Moisture-Stable Iron Racemization Catalyst
    Gustafson, Karl P. J.
    Gudmundsson, Arnar
    Lewis, Kayla
    Backvall, Jan-E.
    CHEMISTRY-A EUROPEAN JOURNAL, 2017, 23 (05) : 1048 - 1051
  • [29] Highly compatible ruthenium and enzyme catalysts for efficient dynamic kinetic resolution of sec-alcohols at ambient temperature:: Insights into the mechanism.
    Martín-Matute, B
    Edin, M
    Bogár, K
    Bäckvall, JE
    ABSTRACTS OF PAPERS OF THE AMERICAN CHEMICAL SOCIETY, 2005, 229 : U582 - U582
  • [30] (S)-selective dynamic kinetic resolution of secondary alcohols by combination of subtilisin and an aminocyclopentadienylruthenium complex as the catalysts.
    Lee, HK
    Kim, MJ
    ABSTRACTS OF PAPERS OF THE AMERICAN CHEMICAL SOCIETY, 2004, 228 : U36 - U36