ASYMMETRIC TRANSESTERIFICATION OF MESO-2,5-DIBROMOADIPATE AND SYNTHESIS OF OPTICALLY-ACTIVE CIS-2,5-DISUBSTITUTED PYRROLIDINES

被引：5
|
作者：
OZASA, N [1 ]
TOKIOKA, K [1 ]
YAMAMOTO, Y [1 ]
机构：
[1] KYOTO UNIV, GRAD SCH HUMAN & ENVIRONM SCI, KYOTO 60601, JAPAN
来源：
BIOSCIENCE BIOTECHNOLOGY AND BIOCHEMISTRY | 1995年 / 59卷 / 10期
关键词：
D O I：
10.1271/bbb.59.1905
中图分类号：
Q5 [生物化学]; Q7 [分子生物学];
学科分类号：
071010 ; 081704 ;
摘要：
Asymmetric trans-esterification of meso-2,5-dibromoadipate to (-)-benzyl methyl 2,5-dibromoadipate by lipase with subsequent chemical reactions afforded optically active cis-2,5-disubstituted pyrrolidines. An equivalent asymmetric transformation was performed by selectively hydrolyzing a cis-2,5-disubstituted pyrrolidine having a chiral N-substituent.
引用
收藏
页码：1905 / 1907
页数：3
相关论文
共 50 条
  • [1] A NEW ROUTE TO OPTICALLY PURE CIS-2,5-DISUBSTITUTED AND TRANS-2,5-DISUBSTITUTED PYRROLIDINES
    JEGHAM, S
    DAS, BC
    TETRAHEDRON LETTERS, 1989, 30 (21) : 2801 - 2804
  • [2] Facile synthetic route to enantiopure unsymmetric cis-2,5-disubstituted pyrrolidines
    Wang, Ping-An
    Xu, Zheng-Shuang
    Chen, Chun-Feng
    Gao, Xu-Guang
    Sun, Xiao-Li
    Zhang, Sheng-Yong
    CHIRALITY, 2007, 19 (07) : 581 - 588
  • [3] A versatile method for the facile synthesis of enantiopure trans- and cis-2,5-disubstituted pyrrolidines
    Wang, Q
    Sasaki, NA
    Riche, C
    Potier, P
    JOURNAL OF ORGANIC CHEMISTRY, 1999, 64 (23): : 8602 - 8607
  • [4] A short asymmetric synthesis of 2,5-disubstituted pyrrolidines
    Katritzky, AR
    Cui, XL
    Yang, BZ
    Steel, PJ
    TETRAHEDRON LETTERS, 1998, 39 (13) : 1697 - 1700
  • [5] Reductive allylation of pyrrole with allylboranes.: Synthesis of trans- and cis-2,5-disubstituted pyrrolidines
    Bubnov, YN
    Klimkina, EV
    Lavrinovich, LI
    Zykov, AY
    Ignatenko, AV
    RUSSIAN CHEMICAL BULLETIN, 1999, 48 (09) : 1696 - 1706
  • [6] Stereoselective Synthesis of cis-2,5-Disubstituted Pyrrolidines via Copper-Catalyzed Cyclization of Alkenes
    Cai, Sai-Hu
    Da, Bing-Chao
    Zhou, Jia-Hui
    Xu, Yun-He
    Loh, Teck-Peng
    CHINESE JOURNAL OF CHEMISTRY, 2016, 34 (11) : 1076 - 1080
  • [7] cis-Selective synthesis of 2,5-disubstituted pyrrolidines
    Hussaini, SR
    Moloney, MG
    TETRAHEDRON LETTERS, 2004, 45 (06) : 1125 - 1127
  • [8] Synthesis of 2,5-disubstituted pyrrolidines
    Pichon, M
    Figadere, B
    TETRAHEDRON-ASYMMETRY, 1996, 7 (04) : 927 - 964
  • [9] ORGN 588-Asymmetric synthesis of cis and trans-2,5-disubstituted pyrrolidines
    Davis, Franklin A.
    Zhang, Junyi
    Qiu, Hui
    Xu, He
    Wu, Yongzhong
    ABSTRACTS OF PAPERS OF THE AMERICAN CHEMICAL SOCIETY, 2007, 234
  • [10] Synthesis and application of chiral cis-2,5-disubstituted pyrrolidine organocatalysts
    Singh, Suraj
    Kumar, Rohtash
    Dubey, Navneet Nandgopal
    Appayee, Chandrakumar
    CHEMICAL COMMUNICATIONS, 2024, 60 (66) : 8768 - 8771
12345