DIASTEREOSELECTIVE LITHIATION OF N-SILYL-PROTECTED (S)-TETRAHYDRO-1H-PYRROLO[1,2-c]IMIDAZOL-3(2H)-ONE

被引：3
|
作者：
Metallinos, Costa [1 ]
Sadraei, Seyed Iraj [1 ]
Zhukovskaya, Nadezda [1 ]
机构：
[1] Brock Univ, Dept Chem, St Catharines, ON L2S 3A1, Canada
来源：
HETEROCYCLES | 2014年 / 88卷 / 01期
基金：
加拿大自然科学与工程研究理事会;
关键词：
Proline Hydantoin; Diastereoselective Reaction; Lithiation; Triethylsilyl Protecting Group; Pyrroloimidazolinone; CATALYZED ALPHA-ARYLATION; DYNAMIC THERMODYNAMIC RESOLUTION; ASYMMETRIC DEPROTONATION; BOC-PYRROLIDINE; ENANTIOSELECTIVE SYNTHESES; PRODUCT STEREOSPECIFICITY; ENANTIOMERIZATION; STEREOSELECTIVITY; SUBSTITUTION; CYCLIZATION;
D O I：
10.3987/COM-13-S(S)29
中图分类号：
O62 [有机化学];
学科分类号：
070303 ; 081704 ;
摘要：
An L-proline-derived imidazolone protected with an N-triethylsilyl (N-TES) group undergoes diastereoselective lithiation-electrophile quench to give C5-substituted products with syn stereochemistry. Unlike the previous N-t-Bu analogues, the N-TES derivatives may be easily N-desilylated to give secondary ureas that serve as precursors to N-phenyl chiral bicyclic guanidines.
引用
收藏
页码：347 / 362
页数：16
相关论文
共 50 条
  • [1] Synthesis of phosphodiesterase IVb inhibitors 2. Stereoselective synthesis of hexahydro-3H-pyrrolo[1,2-c]imidazol-3-one and tetrahydro-1H-pyrrolo[1,2-c][1,3]oxazol-3-one derivatives
    Zhmurov, P. A.
    Tabolin, A. A.
    Sukhorukov, A. Yu.
    Lesiv, A. V.
    Klenov, M. S.
    Khomutova, Yu. A.
    Ioffe, S. L.
    Tartakovsky, V. A.
    RUSSIAN CHEMICAL BULLETIN, 2011, 60 (11) : 2390 - 2395
  • [2] Synthesis of phosphodiesterase IVb inhibitors 2. Stereoselective synthesis of hexahydro-3H-pyrrolo[1,2-c]imidazol-3-one and tetrahydro-1H-pyrrolo[1,2-c][1,3]oxazol-3-one derivatives
    P. A. Zhmurov
    A. A. Tabolin
    A. Yu. Sukhorukov
    A. V. Lesiv
    M. S. Klenov
    Yu. A. Khomutova
    S. L. Ioffe
    V. A. Tartakovsky
    Russian Chemical Bulletin, 2011, 60 : 2390 - 2395
  • [3] Syntheses of optically active tetrahydro-1H-pyrrolo[1,2-a]imidazol-2-ones and hexahydroimidazo[1,2-α]pyridin-2(3H)-ones
    Katritzky, AR
    He, HY
    Wang, J
    JOURNAL OF ORGANIC CHEMISTRY, 2002, 67 (14): : 4951 - 4956
  • [4] SYNTHESIS OF 3H-PYRROLO[1,2-C]IMIDAZOLE-3,5(2H)-DIONES
    SHAW, KJ
    VARTANIAN, M
    JOURNAL OF ORGANIC CHEMISTRY, 1991, 56 (02): : 858 - 861
  • [5] Chemoselective synthesis of biheterocyclic skeletons tetrahydro-1H-pyrrolo[1,2-c]imidazole and tetrahydropyrrolo[1,2-c]thiazole derivatives via multicomponent self-sorting domino strategy
    Cai, Qun
    Jia, Feng-Cheng
    Li, Deng-Kui
    Xu, Cheng
    Ding, Ke-Rong
    Wu, An-Xin
    TETRAHEDRON, 2015, 71 (36) : 6104 - 6111
  • [6] Novel synthesis of tetrahydro-1H-pyrrolo[1,2-a]imidazol-2-ones via decarboxylative cyclization reaction of α-amino acids and α-ketoamides
    Wu, Jia-shou
    Jiang, Hua-jiang
    Yang, Jian-guo
    Jin, Zheng-neng
    Chen, Ding-ben
    TETRAHEDRON LETTERS, 2017, 58 (06) : 546 - 551
  • [7] Synthesis of novel 16-spiro steroids: 7-(Aryl)tetrahydro-1H-pyrrolo[1,2-c][1,3]thiazolo estrone hybrid heterocycles
    Jeyachandran, Veerappan
    Kumar, Sundaravel Vivek
    Kumar, Raju Ranjith
    STEROIDS, 2014, 82 : 29 - 37
  • [8] Discovery of fused bicyclic derivatives of 1H-pyrrolo[1,2-c]imidazol-1-one as VDR signaling regulators
    Xu, Bin
    Ding, Mo-Yu
    Weng, Zhibing
    Li, Zheng-Qing
    Li, Feng
    Sun, Xia
    Chen, Qiu-Ling
    Wang, Yi-Tao
    Wang, Ying
    Zhou, Guo-Chun
    BIOORGANIC & MEDICINAL CHEMISTRY, 2019, 27 (17) : 3879 - 3888
  • [9] Selective Synthesis using ETFBO: A New Strategy for the Preparation of Hexahydro-1H-pyrrolo[1,2-c]imidazol-1-one.
    Faillace, Martin S.
    Ceballos, Noelia M.
    Shustova, Natalia B.
    Pelaez, Walter J.
    ASIAN JOURNAL OF ORGANIC CHEMISTRY, 2023, 12 (08)
  • [10] SYNTHESIS OF 5(H)-ARYLINDENO[1,2-C]PYRIDAZIN-3(2H)-ONES
    OMAR, MT
    EID, ME
    INDIAN JOURNAL OF CHEMISTRY SECTION B-ORGANIC CHEMISTRY INCLUDING MEDICINAL CHEMISTRY, 1981, 20 (12): : 1097 - 1099
12345