Epoxides to α-Mercapto-γ-lactones via Ionic Liquid Promoted Mercaptoacetylative Ring-Opening-Ring-Closing Cascade

被引：23
|
作者：
Patel, Rajesh [1 ]
Srivastava, Vishnu P. [1 ]
Yadav, Lal Dhar S. [1 ]
机构：
[1] Univ Allahabad, Dept Chem, Green Synth Lab, Allahabad 211002, Uttar Pradesh, India
来源：
SYNLETT | 2010年 / 12期
关键词：
gamma-lactones; epoxides; ionic liquids; cascade reactions; translactonization; stereoselective synthesis; ENANTIOSELECTIVE SYNTHESIS; ONE-POT; CYCLIZATION; ACID; METATHESIS; EFFICIENT; ESTERS; TRANSFORMATIONS; BUTYROLACTONES; COMPLEXES;
D O I：
10.1055/s-0030-1258121
中图分类号：
O62 [有机化学];
学科分类号：
070303 ; 081704 ;
摘要：
Task-specific ionic liquid promoted {[Bmim]OH} one-pot synthesis of alpha-mercapto-gamma-lactones is reported. The present protocol involves regioselective epoxide ring opening and intramolecular translactonisation cascade. A variety of epoxides undergo this ring-opening-ring-closing cascade with 2-methyl-2-phenyl-1,3-oxathiolan-5-one to afford alpha-mercapto-gamma-lactones diastereoselectively in good to excellent yields. After isolation of the product, the ionic liquid [Bmim]OH could be easily recovered and reused without any loss of efficiency.
引用
收藏
页码：1797 / 1802
页数：6
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  • [1] Efficient synthesis of chlorohydrins: ionic liquid promoted ring-opening reaction of epoxides and TMSCl
    Xu, LW
    Li, L
    Xia, CG
    Zhao, PQ
    [J]. TETRAHEDRON LETTERS, 2004, 45 (11) : 2435 - 2438
  • [2] Iron Promoted Ring Opening and Ring Closing Cascade (ROCC) Reaction of Ortho-Carboxy-Isoxazoles Leading to Isoindolinone Derivatives
    Gudipati, Ramakrishna
    Jayaram, Vankudoth
    Raghavulu, Karri
    Bhoot, Dinesh
    Basavaiah, Keloth
    Yennam, Satyanarayana
    Behera, Manoranjan
    [J]. EUROPEAN JOURNAL OF ORGANIC CHEMISTRY, 2021, 2021 (37) : 5127 - 5134
  • [3] Ring opening of chalcone epoxides in a Lewis acidic ionic liquid via intramolecular Friedel-Crafts alkylation
    Canfield, Amanda
    Manchanayakage, Renuka
    [J]. ABSTRACTS OF PAPERS OF THE AMERICAN CHEMICAL SOCIETY, 2018, 255
  • [4] Concise Formal Synthesis of Porothramycins A and B via Zincke Pyridinium Ring-Opening/Ring-Closing Cascade
    Michels, Theo D.
    Kier, Matthew J.
    Kearney, Aaron M.
    Vanderwal, Christopher D.
    [J]. ORGANIC LETTERS, 2010, 12 (13) : 3093 - 3095
  • [5] Task specific ionic liquid as solvent, catalyst and reagent for regioselective ring opening of epoxides in water
    Nezhad, Eshagh Rezaee
    Sajjadifar, Sami
    Heidarizadeh, Fariba
    Karimian, Saaid
    [J]. ARABIAN JOURNAL OF CHEMISTRY, 2019, 12 (08) : 2098 - 2103
  • [6] W(OTf)6-Catalyzed Synthesis of γ-Lactones by Ring Contraction of Macrolides or Ring Closing of Terminal Hydroxyfatty Acids in Ionic Liquid
    Xie, Zhong-Yu
    Deng, Jin
    Fu, Yao
    [J]. CHEMSUSCHEM, 2018, 11 (14) : 2332 - 2339
  • [7] Efficient Ring Opening of Protected and Unprotected Aziridines Promoted by Stable Zinc Selenolate in Ionic Liquid
    Salman, Syed M.
    Schwab, Ricardo S.
    Alberto, Eduardo E.
    Vargas, Josimar
    Dornelles, Luciano
    Rodrigues, Oscar E. D.
    Braga, Antonio L.
    [J]. SYNLETT, 2011, (01) : 69 - 72
  • [8] Epoxide ring-opening reaction promoted by ionic liquid reactivity: interplay of experimental and theoretical studies
    Chen, Shengxin
    Zeng, Guixiang
    Li, Yingwei
    He, Bin
    Liu, Ruixia
    Zhang, Suojiag
    [J]. CATALYSIS SCIENCE & TECHNOLOGY, 2019, 9 (20) : 5567 - 5571
  • [9] Acetic acid functionalized ionic liquid systems: An efficient and recyclable catalyst for the regioselective ring opening of epoxides with NaN3
    Rezayati, Sobhan
    Salehi, Elaheh
    Hajinasiri, Rahimeh
    Abad, Saeid Afshari Sharif
    [J]. COMPTES RENDUS CHIMIE, 2017, 20 (05) : 554 - 558
  • [10] Masked amino acid: a new C-nucleophile for I2-catalyzed stereoselective ring opening of epoxides in ionic liquid
    Rai, Vijai K.
    Sharma, Roopali
    Kumar, Anil
    [J]. TETRAHEDRON LETTERS, 2013, 54 (09) : 1071 - 1075
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