Enantioselective enzymatic desymmetrization of prochiral 1,3-diols and enzymatic resolution of monoprotected 1,3-diols based on α-tetralone and related multifunctional scaffolds

被引：12
|
作者：
Mahapatra, Tridib [1 ]
Das, Tapas [1 ]
Nanda, Samik [1 ]
机构：
[1] Indian Inst Technol, Dept Chem, Kharagpur 721302, W Bengal, India
来源：
TETRAHEDRON-ASYMMETRY | 2008年 / 19卷 / 21期
关键词：
D O I：
10.1016/j.tetasy.2008.10.024
中图分类号：
O61 [无机化学];
学科分类号：
070301 ; 081704 ;
摘要：
Novel multifunctional chemotypes based on alpha-tetralone, alpha-indarione, and chromanone have been synthesized by a chemo-enzymatic approach by applying an enzymatic irreversible transesterification strategy. The scaffolds synthesized can be further elaborated with subsequent enzymatic as well as chemical transformations for the generation of new sets of structurally related organic molecules. (C) 2008 Elsevier Ltd. All rights reserved.
引用
收藏
页码：2497 / 2507
页数：11
相关论文
共 50 条
  • [1] Enantioselective Desymmetrization of 1,3-Diols by a Chiral DMAP Derivative
    Mandai, Hiroki
    Ashihara, Kosuke
    Mitsudo, Koichi
    Suga, Seiji
    CHEMISTRY LETTERS, 2018, 47 (11) : 1360 - 1363
  • [2] ENZYMATIC PREPARATION OF ENANTIOMERICALLY PURE AND SELECTIVELY PROTECTED 1,2-DIOLS AND 1,3-DIOLS
    GOERGENS, U
    SCHNEIDER, MP
    JOURNAL OF THE CHEMICAL SOCIETY-CHEMICAL COMMUNICATIONS, 1991, (16) : 1066 - 1068
  • [3] ACETALS AND KETALS OF 1,3-DIOLS
    CONRAD, WE
    CONRAD, HM
    GESNER, BD
    LEVASSEUR, LA
    MURPHY, RF
    JOURNAL OF ORGANIC CHEMISTRY, 1961, 26 (09): : 3571 - &
  • [4] Stereoselective synthesis of 1,3-diols
    Bode, SE
    Wolberg, M
    Müller, M
    SYNTHESIS-STUTTGART, 2006, (04): : 557 - 588
  • [5] Enantioselective Medium-Ring Lactone Synthesis through an NHC-Catalyzed Intramolecular Desymmetrization of Prochiral 1,3-Diols
    Wu, Zijun
    Wang, Jian
    ACS CATALYSIS, 2017, 7 (11): : 7647 - 7652
  • [6] Gold( I)-Catalyzed Enantioselective Desymmetrization of 1,3-Diols through Intramolecular Hydroalkoxylation of Allenes
    Zi, Weiwei
    Toste, F. Dean
    ANGEWANDTE CHEMIE-INTERNATIONAL EDITION, 2015, 54 (48) : 14447 - 14451
  • [7] ENZYME-CATALYZED RESOLUTION OF 1,3-DIARYLPROPAN-1,3-DIOLS
    LEVAYER, F
    RABILLER, C
    TELLIER, C
    TETRAHEDRON-ASYMMETRY, 1995, 6 (07) : 1675 - 1682
  • [8] Synthesis of cyclic 1,3-diols as scaffolds for spatially directed libraries
    Singh, Gurpreet
    Aube, Jeffrey
    ORGANIC & BIOMOLECULAR CHEMISTRY, 2016, 14 (18) : 4299 - 4303
  • [9] Deracemization by enantiodifferentiating inversion in 1,3-diols
    Davis, AP
    ANGEWANDTE CHEMIE-INTERNATIONAL EDITION IN ENGLISH, 1997, 36 (06): : 591 - 594
  • [10] Production of 1,3-diols in Escherichia coli
    Kataoka, Naoya
    Vangnai, Alisa S.
    Pongtharangkul, Thunyarat
    Yakushi, Toshiharu
    Matsushita, Kazunobu
    BIORESOURCE TECHNOLOGY, 2017, 245 : 1538 - 1541
12345