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
  • [31] A HIGHLY EFFICIENT KINETIC RESOLUTION OF OMEGA-TRIMETHYLSILYL POLYUNSATURATED SECONDARY ALCOHOLS BY LIPASE-CATALYZED TRANSESTERIFICATION
    Fiandanese, V
    Hassan Omar, O
    Naso, F
    Scilimati, A
    SYNLETT, 1993, (07) : 491 - 493
  • [32] Rapid Synthesis of Cobalt Nitride Nanowires: Highly Efficient and Low-Cost Catalysts for Oxygen Evolution
    Zhang, Yongqi
    Ouyang, Bo
    Xu, Jing
    Jia, Guichong
    Chen, Shi
    Rawat, Rajdeep Singh
    Fan, Hong Jin
    ANGEWANDTE CHEMIE-INTERNATIONAL EDITION, 2016, 55 (30) : 8670 - 8674
  • [33] ORGN 429-Fast racemization of chiral amines and alcohols using half-sandwich iridacycle catalysts and application to dynamic kinetic resolution
    Jerphagnon, Thomas
    Haak, Robert
    Berthiol, Florian
    Gayet, Arnaud
    Feringa, Ben L.
    de Vries, Johannes G.
    ABSTRACTS OF PAPERS OF THE AMERICAN CHEMICAL SOCIETY, 2009, 237
  • [34] Nano-layered manganese oxides as low-cost, easily synthesized, environmentally friendly and efficient catalysts for epoxidation of olefins
    Amini, Mojtaba
    Najafpour, Mohammad Mahdi
    Nayeri, Sara
    Pashaei, Babak
    Bagherzadeh, Mojtaba
    RSC ADVANCES, 2012, 2 (09) : 3654 - 3657
  • [35] New air-stable iron catalyst for efficient dynamic kinetic resolution of secondary benzylic and aliphatic alcohols
    Yang, Qiong
    Zhang, Na
    Liu, Mingke
    Zhou, Shaolin
    TETRAHEDRON LETTERS, 2017, 58 (25) : 2487 - 2489
  • [36] Thermoresponsive chiral salen Mn(III) complexes as efficient and reusable catalysts for the oxidative kinetic resolution of secondary alcohols in water
    Tan, Rong
    Dong, Yan
    Peng, Ming
    Zheng, Weiguo
    Yin, Donghong
    APPLIED CATALYSIS A-GENERAL, 2013, 458 : 1 - 10
  • [37] Non-Enzymatic Dynamic Kinetic Resolution of Secondary Aryl Alcohols: Planar Chiral Ferrocene and Ruthenium Catalysts in Cooperation
    Diaz-Alvarez, Alba E.
    Mesas-Sanchez, Laura
    Diner, Peter
    ANGEWANDTE CHEMIE-INTERNATIONAL EDITION, 2013, 52 (02) : 502 - 504
  • [38] Easily available, low-cost 9,9′-bianthracene derivatives as efficient blue hosts and deep-blue emitters in OLEDs
    Li, Zhanfeng
    Gan, Guoyue
    Ling, Zhitian
    Guo, Kunping
    Si, Changfeng
    Lv, Xiang
    Wang, Hua
    Wei, Bin
    Hao, Yuying
    ORGANIC ELECTRONICS, 2019, 66 : 24 - 31
  • [39] Formic Acid: A Low-Cost, Mild, Ecofriendly, and Highly Efficient Catalyst for the Rapid Synthesis of β-Enaminones
    Patil, Siddappa A.
    Medina, Phillip A.
    Gonzalez-Flores, Diego
    Vohs, Jason K.
    Dever, Seth
    Pineda, Leslie W.
    Montero, Mavis L.
    Fahlman, Bradley D.
    SYNTHETIC COMMUNICATIONS, 2013, 43 (17) : 2349 - 2364
  • [40] A HIGHLY EFFICIENT KINETIC RESOLUTION OF GAMMA-TRIMETHYLSILYL AND BETA-TRIMETHYLSILYL SECONDARY ALLYLIC ALCOHOLS BY THE SHARPLESS ASYMMETRIC EPOXIDATION
    KITANO, Y
    MATSUMOTO, T
    SATO, F
    TETRAHEDRON, 1988, 44 (13) : 4073 - 4086