Nonenzymatic Dynamic Kinetic Resolution of α-(Arylthio)- and α-(Alkylthio) alkanoic Acids

被引:46
|
作者
Yang, Xing [1 ]
Birman, Vladimir B. [1 ]
机构
[1] Washington Univ, Dept Chem, St Louis, MO 63130 USA
基金
美国国家科学基金会;
关键词
acyl-transfer catalysis; kinetic resolution; organocatalysis; racemization; synthetic methods; DUAL-FUNCTION CATALYSIS; ASYMMETRIC-SYNTHESIS; AMINO-ACIDS; ENZYMATIC RESOLUTION; ACHIRAL ALCOHOLS; CARBOXYLIC-ACIDS; ALPHA-ARYL; SULFENYLATION; DERIVATIVES; HOMOBENZOTETRAMISOLE;
D O I
10.1002/anie.201007860
中图分类号
O6 [化学];
学科分类号
0703 ;
摘要
Dynamic solution: The title acids undergo dynamic kinetic resolution during an enantioselective esterification catalyzed by (S)-homobenzotetramisole ((S)-HBTM; see scheme). This method extends the scope of the carboxylic acid derivatives that are amenable to the nonenzymatic version of this transformation. Copyright © 2011 WILEY-VCH Verlag GmbH & Co. KGaA, Weinheim.
引用
收藏
页码:5553 / 5555
页数:3
相关论文
共 50 条
  • [31] Enantioselective Synthesis of α-Thiocarboxylic Acids by Nitrilase Biocatalysed Dynamic Kinetic Resolution of α-Thionitriles
    Lauder, Kate
    Anselmi, Silvia
    Finnigan, James D.
    Qi, Yuyin
    Charnock, Simon J.
    Castagnolo, Daniele
    CHEMISTRY-A EUROPEAN JOURNAL, 2020, 26 (46) : 10422 - 10426
  • [32] Stereoselective Synthesis of β-Branched Aromatic α-Amino Acids by Biocatalytic Dynamic Kinetic Resolution**
    Li, Fuzhuo
    Yang, Li-Cheng
    Zhang, Jingyang
    Chen, Jason S.
    Renata, Hans
    ANGEWANDTE CHEMIE-INTERNATIONAL EDITION, 2021, 60 (32) : 17680 - 17685
  • [33] Recent Advances in (Dynamic) Kinetic Resolution and Desymmetrization Catalyzed by Chiral Phosphoric Acids
    Liu, Wei
    Yang, Xiaoyu
    ASIAN JOURNAL OF ORGANIC CHEMISTRY, 2021, 10 (04) : 692 - 710
  • [34] Dynamic Kinetic Resolution of Amines and Amino Acids by Enzyme-Metal Cocatalysis
    Kim, Yunwoong
    Park, Jaiwook
    Kim, Mahn-Joo
    CHEMCATCHEM, 2011, 3 (02) : 271 - 277
  • [35] Dynamic kinetic resolution of 2-arylpropanoic acids via the asymmetric esterification
    Ono, Keisuke
    Nakata, Kenya
    Shiina, Isamu
    ABSTRACTS OF PAPERS OF THE AMERICAN CHEMICAL SOCIETY, 2012, 244
  • [36] Chemical Dynamic Kinetic Resolution and S/R Interconversion of Unprotected α-Amino Acids
    Takeda, Ryosuke
    Kawamura, Akie
    Kawashima, Aki
    Sato, Tatsunori
    Moriwaki, Hiroki
    Izawa, Kunisuke
    Akaji, Kenichi
    Wang, Shuni
    Liu, Hong
    Luis Acena, Jose
    Soloshonok, Vadim A.
    ANGEWANDTE CHEMIE-INTERNATIONAL EDITION, 2014, 53 (45) : 12214 - 12217
  • [37] Comparative study of different chiral ligands for dynamic kinetic resolution of amino acids
    Nagaoka, Keita
    Nakano, Arina
    Han, Jianlin
    Sakamoto, Tsubasa
    Konno, Hiroyuki
    Moriwaki, Hiroki
    Abe, Hidenori
    Izawa, Kunisuke
    Soloshonok, Vadim A.
    CHIRALITY, 2021, 33 (10) : 685 - 702
  • [38] Nonenzymatic kinetic resolution of racemic alcohols through an ''induced fit'' process
    Kawabata, T
    Nagato, M
    Takasu, K
    Fuji, K
    JOURNAL OF THE AMERICAN CHEMICAL SOCIETY, 1997, 119 (13) : 3169 - 3170
  • [39] Nonenzymatic kinetic resolution of 3-hydroxyalkanamides with chiral copper catalyst
    Demizu, Yosuke
    Kubo, Yuki
    Matsumura, Yoshihiro
    Onomura, Osamu
    SYNLETT, 2008, (03) : 433 - 437