Hydrolytic dynamic kinetic resolution of racemic 3-phenyl-2-oxetanone to chiral tropic acid

被引：3
|
作者：
Kawasaki, Midori [1 ]
Shirai, Takahiro [2 ]
Yatsuzuka, Kenji [1 ]
Shirai, Ryuichi [1 ]
机构：
[1] Doshisha Womens Coll Liberal Arts, Fac Pharmaceut Sci, 97-1 Minamihokotate, Kyoto 6100395, Japan
[2] Hiroshima Univ, Grad Sch Biomed & Hlth Sci, 1-2-3 Kasumi,Minami-ku, Hiroshima 7348553, Japan
来源：
RSC ADVANCES | 2024年 / 14卷 / 09期
关键词：
DERIVATIVES; SERINE; ESTERS;
D O I：
10.1039/d3ra08594e
中图分类号：
O6 [化学];
学科分类号：
0703 ;
摘要：
Tropic acid was synthesized in a good yield and with high enantioselectivity (81% ee) under non-biphasic conditions via the novel hydrolytic dynamic kinetic resolution of racemic 3-phenyl-2-oxetanone (tropic acid beta-lactone) in the presence of a chiral quaternary ammonium phase-transfer catalyst and strongly basic anion exchange resin as the hydroxide ion donor. The hydrolytic dynamic kinetic resolution of racemic 3-phenyl-2-oxetanone using a chiral PTC and water-free basic anion exchange resin as the hydroxide ion donor was achieved.
引用
收藏
页码：6121 / 6126
页数：6
相关论文
共 50 条
  • [21] 4-carboxy-2-oxetanone as a new chiral precursor in the preparation of functionalized racemic or optically active poly(malic acid) derivatives
    LeboucherDurand, MA
    Langlois, V
    Guerin, P
    POLYMER BULLETIN, 1996, 36 (01) : 35 - 41
  • [22] Chiral Guanidine Catalyzed Acylative Kinetic Resolution of Racemic 2-Bromo-l-arylethanols
    Sawada, Erika
    Nakata, Kenya
    CHEMISTRY LETTERS, 2021, 50 (02) : 371 - 373
  • [23] Highly enantioselective dynamic kinetic resolution and desymmetrization processes by cyclocondensation of chiral aminoalcohols with racemic or prochiral δ-oxoacid derivatives
    Amat, M
    Bassas, O
    Pericàs, MA
    Pastó, M
    Bosch, J
    CHEMICAL COMMUNICATIONS, 2005, (10) : 1327 - 1329
  • [24] Palladium- and Rhodium-Catalyzed Dynamic Kinetic Resolution of Racemic Internal Allenes Towards Chiral Pyrazoles
    Hilpert, Lukas J.
    Sieger, Simon V.
    Haydl, Alexander M.
    Breit, Bernhard
    ANGEWANDTE CHEMIE-INTERNATIONAL EDITION, 2019, 58 (11) : 3378 - 3381
  • [25] Dynamic kinetic resolution of racemic N-phthalyl amino acids using (S)-α-methylpantolactone as the chiral auxiliary
    Calmes, M
    Glot, C
    Michel, T
    Rolland, M
    Martinez, J
    TETRAHEDRON-ASYMMETRY, 2000, 11 (03) : 737 - 741
  • [26] Rhodium-Catalyzed Dynamic Kinetic Resolution of Racemic Internal Allenes towards Chiral Allylated Triazoles and Tetrazoles
    Sieger, Simon, V
    Lubins, Ilja
    Breit, Bernhard
    CATALYSTS, 2022, 12 (10)
  • [27] A NEW ENANTIOSELECTIVE SYNTHESIS OF GLYCIDATES VIA DYNAMIC KINETIC RESOLUTION OF RACEMIC 2-CHLORO-3-KETO ESTERS USING CHIRAL RU(II) COMPLEXES
    GENET, JP
    DEANDRADE, MCC
    RATOVELOMANANAVIDAL, V
    TETRAHEDRON LETTERS, 1995, 36 (12) : 2063 - 2066
  • [28] Chiral BrOnsted Acid Catalyzed Dynamic Kinetic Asymmetric Hydroamination of Racemic Allenes and Asymmetric Hydroamination of Dienes
    Lin, Jin-Shun
    Li, Tao-Tao
    Jiao, Guan-Yuan
    Gu, Qiang-Shuai
    Cheng, Jiang-Tao
    Lv, Ling
    Liu, Xin-Yuan
    ANGEWANDTE CHEMIE-INTERNATIONAL EDITION, 2019, 58 (21) : 7092 - 7096
  • [29] SYNTHETIC CONTROL BASED ON CHIRAL 2-HALOPYRIDINIUM SALTS .2. KINETIC RESOLUTION OF RACEMIC AMINES
    MUKAIYAMA, T
    ONAKA, M
    SHIONO, M
    CHEMISTRY LETTERS, 1977, (06) : 651 - 654
  • [30] Hydrolytic kinetic resolution of racemic terminal epoxides catalyzed by Co(III) (Salen) possessing no C2-symmetry
    Li, XS
    Shen, ZX
    Zhang, YW
    CHINESE JOURNAL OF ORGANIC CHEMISTRY, 2002, 22 (05) : 327 - 330
12345