Kinetic Resolution of Racemic Carboxylic Acids Using Achiral Alcohols by the Promotion of Benzoic Anhydrides and Tetramisole Derivatives: Production of Chiral Nonsteroidal Anti-Inflammatory Drugs and Their Esters

被引：60
|
作者：
Shiina, Isamu [1 ]
Nakata, Kenya [1 ]
Onda, Yu-suke [1 ]
机构：
[1] Tokyo Univ Sci Kagurazaka, Fac Sci, Dept Appl Chem, Shinjuku Ku, Tokyo 1628601, Japan
来源：
EUROPEAN JOURNAL OF ORGANIC CHEMISTRY | 2008年 / 2008卷 / 35期
关键词：
Kinetic resolution; Carboxylic acids; Anhydrides;
D O I：
10.1002/ejoc.200800942
中图分类号：
O62 [有机化学];
学科分类号：
070303 ; 081704 ;
摘要：
A variety of optically active carboxylic esters were produced by kinetic resolution of racemic carboxylic acids by using achiral alcohols, benzoic anhydrides, and Birman's tetramisole-type catalysts. Bis(alpha-naphthyl)methanol is a very effective reagent for producing the corresponding esters with high ee values in the presence of 4-methoxybenzoic anhydride (PMBA) as the coupling reagent by promotion of benzotetramisole derivatives (BTM, alpha-Np-BTM, and beta-Np-BTM). This protocol directly provides chiral carboxylic esters from free carboxylic acids and achiral alcohols by utilizing a transacylation process to generate the mixed anhydrides from the acid components with benzoic anhydride derivatives in the presence of chiral catalysts. ((C) Wiley-VCH Verlag GmbH & Co. KGaA, 69451 Weinheim, Germany, 2008)
引用
收藏
页码：5887 / 5890
页数：4
相关论文
共 8 条
  • [1] The first asymmetric esterification of free carboxylic acids with racemic alcohols using benzoic anhydrides and tetramisole derivatives: an application to the kinetic resolution of secondary benzylic alcohols
    Shiina, Isamu
    Nakata, Kenya
    TETRAHEDRON LETTERS, 2007, 48 (47) : 8314 - 8317
  • [2] Kinetic Resolution of Racemic α-Arylalkanoic Acids with Achiral Alcohols via the Asymmetric Esterification Using Carboxylic Anhydrides and Acyl-Transfer Catalysts
    Shiina, Isamu
    Nakata, Kenya
    Ono, Keisuke
    Onda, Yu-suke
    Itagak, Makoto
    JOURNAL OF THE AMERICAN CHEMICAL SOCIETY, 2010, 132 (33) : 11629 - 11641
  • [3] Non-enzymatic dynamic kinetic resolution of racemic α-arylalkanoic acids: an advanced asymmetric synthesis of chiral nonsteroidal anti-inflammatory drugs (NSAIDs)
    Shiina, Isamu
    Ono, Keisuke
    Nakata, Kenya
    CATALYSIS SCIENCE & TECHNOLOGY, 2012, 2 (11) : 2200 - 2205
  • [4] Dynamic Kinetic Resolution of Carboxylic Esters Catalyzed by Chiral PPY N-Oxides: Synthesis of Nonsteroidal Anti-Inflammatory Drugs and Mechanistic Insights
    Xie, Ming-Sheng
    Li, Ning
    Tian, Yin
    Wu, Xiao-Xia
    Deng, Yun
    Qu, Gui-Rong
    Guo, Hai-Ming
    ACS CATALYSIS, 2021, 11 (13) : 8183 - 8196
  • [5] Kinetic resolution of racemic α-hydroxyphosphonates by asymmetric esterification using achiral carboxylic acids with pivalic anhydride and a chiral acyl-transfer catalyst
    Shiina, Isamu
    Ono, Keisuke
    Nakahara, Takayoshi
    CHEMICAL COMMUNICATIONS, 2013, 49 (91) : 10700 - 10702
  • [6] The Effect of the Stationary Phase on Resolution in the HPLC-Based Separation of Racemic Mixtures Using Vancomycin as a Chiral Selector: A Case Study with Profen Nonsteroidal Anti-Inflammatory Drugs
    Gherdaoui, Dehbiya
    Yahoum, Madiha Melha
    Toumi, Selma
    Tahraoui, Hichem
    Bouazza, Fatma
    Lefnaoui, Sonia
    Zeghdaoui, Abdelhamid
    Amrane, Abdeltif
    Jaouadi, Bassem
    Zhang, Jie
    SYMMETRY-BASEL, 2023, 15 (12):
  • [7] KINETIC RESOLUTION OF THE RACEMIC 1-(ARYLOXAZOL-2-YL)CARBINOLS WITH ACHIRAL CARBOXYLIC ACIDS BY ASYMMETRIC ESTERIFICATION: A NEW METHOD FOR THE PREPARATION OF CHIRAL 1,2-AMINO ALCOHOLS
    Nakata, Kenya
    Ono, Keisuke
    Shiina, Isamu
    HETEROCYCLES, 2011, 82 (02) : 1171 - +
  • [8] An effective kinetic resolution of racemic α-arylpropanoic acids, α-arylbutanoic acids, and β-substituted-α-arylpropanoic acids with bis(9-phenanthryl)methanol as a new achiral nucleophile in the asymmetric esterification using carboxylic anhydrides and the acyl-transfer catalyst
    Nakata, Kenya
    Onda, Yu-suke
    Ono, Keisuke
    Shiina, Isamu
    TETRAHEDRON LETTERS, 2010, 51 (43) : 5666 - 5669
1