An effective protocol for the synthesis enantiomerically pure 4-substituted oxetane-2-ones

被引:8
|
作者
Balakier, Tomasz [1 ]
Chaladaj, Wojciech [1 ]
Jurczak, Janusz [1 ]
Adamus, Grazyna [2 ]
Kowalczuk, Marek [2 ]
机构
[1] Polish Acad Sci, Inst Organ Chem, PL-01224 Warsaw, Poland
[2] Polish Acad Sci, Ctr Polymer & Carbon Mat, PL-41819 Zabrze, Poland
关键词
Epoxide kinetic resolution; Carbonylation; beta-Lactones; Gram-scale synthesis; EPOXIDE CARBONYLATION; BETA-LACTONES; CATALYST; POLYMERIZATION; COMPLEXES;
D O I
10.1016/j.tet.2013.04.020
中图分类号
O62 [有机化学];
学科分类号
070303 ; 081704 ;
摘要
Six enantiomerically pure 4-substituted oxetane-2-ones (beta-lactones) were obtained using the known Jacobsen's catalytic hydrolytic resolution of racemic epoxides, followed by atmospheric pressure carbonylation reaction. (C) 2013 Elsevier Ltd. All rights reserved.
引用
收藏
页码:4990 / 4993
页数:4
相关论文
共 50 条
  • [21] ASYMMETRIC-SYNTHESIS WITH CHIRAL HYDROXYLAMINES - SYNTHESIS OF OPTICALLY PURE 4-SUBSTITUTED AZETIDINONES
    BALDWIN, SW
    AUBE, J
    TETRAHEDRON LETTERS, 1987, 28 (02) : 179 - 182
  • [22] Synthesis of Enantiomerically Pure 4-Hydroxy-2-cyclopentenones
    Kumaraguru, Thenkrishnan
    Babita, Panuganti
    Sheelu, Gurrala
    Lavanya, Kuna
    Fadnavis, Nitin W.
    ORGANIC PROCESS RESEARCH & DEVELOPMENT, 2013, 17 (12) : 1526 - 1530
  • [23] 4-substituted azetidin-2-ones, new building blocks for the synthesis of beta-lactams
    Kaluza, Z
    Park, SH
    SYNLETT, 1996, (09) : 895 - &
  • [24] Facile synthesis of 4-substituted 2-pyrazolin-5-ones under phase transfer catalysis
    Shiba, SA
    Harb, NMS
    ElKassaby, MA
    Hassan, MA
    AbouElRegal, MMK
    PHOSPHORUS SULFUR AND SILICON AND THE RELATED ELEMENTS, 1995, 104 (1-4): : 15 - 20
  • [25] SYNTHESIS OF 4-SUBSTITUTED ARSABENZENES
    ABUORABI, ST
    ASHE, AJ
    JOURNAL OF THE UNIVERSITY OF KUWAIT-SCIENCE, 1989, 16 (02): : 269 - 279
  • [26] SYNTHESIS OF 4-SUBSTITUTED DIHYDRORESORCINOLS
    KOST, AN
    OVSENEVA, LG
    JOURNAL OF GENERAL CHEMISTRY USSR, 1962, 32 (12): : 3908 - &
  • [27] Synthesis of 4-Substituted Bisnaphthalimides
    D. G. Kupriyan
    V. F. Anikin
    A. Merz
    L. D. Pantsenker
    Russian Journal of Organic Chemistry, 2004, 40 : 699 - 704
  • [28] ASYMMETRIC-SYNTHESIS VIA CHIRAL HYDROXYLAMINES - SYNTHESIS OF OPTICALLY PURE 4-SUBSTITUTED 2-AZETIDINONES
    BALDWIN, SW
    AUBE, J
    ABSTRACTS OF PAPERS OF THE AMERICAN CHEMICAL SOCIETY, 1983, 186 (AUG): : 179 - ORGN
  • [29] Synthesis of 4-substituted bisnaphthalimides
    Kupriyan, DG
    Anikin, VF
    Merz, A
    Pantsenker, LD
    RUSSIAN JOURNAL OF ORGANIC CHEMISTRY, 2004, 40 (05) : 699 - 704
  • [30] SYNTHESIS OF 4-SUBSTITUTED THIACYCLOHEXANES
    VOLYNSKII, NP
    SHCHERBAKOVA, LP
    BULLETIN OF THE ACADEMY OF SCIENCES OF THE USSR DIVISION OF CHEMICAL SCIENCE, 1979, 28 (05): : 1006 - 1009