Efficient synthesis of β-hydroxy sulfides by microwave-promoted ring opening in (+)-3-carene trans-epoxide with sodium thiolates

被引：5
|
作者：
Agafontsev, Alexander M. [1 ]
Gorshkov, Nikolay B. [1 ]
Tkachev, Alexey V. [1 ,2 ]
机构：
[1] Russian Acad Sci, NN Vorozhtsov Novosibirsk Inst Organ Chem, Siberian Branch, Novosibirsk 630090, Russia
[2] Novosibirsk State Univ, Dept Nat Sci, Novosibirsk 630090, Russia
来源：
MENDELEEV COMMUNICATIONS | 2011年 / 21卷 / 04期
基金：
俄罗斯基础研究基金会;
关键词：
3-CARENE OXIDES; SULFOXIDES; THIOLYSIS;
D O I：
10.1016/j.mencom.2011.07.006
中图分类号：
O6 [化学];
学科分类号：
0703 ;
摘要：
Reaction of (+)-3-carene trans-epoxide with sodium thiolates in methanolic solution in a microwave oven at 140 degrees C for 35-40 min affords corresponding (1S,3S,4S,6R)-4-sulfanylcaran-3-ols in 75-95% yields.
引用
收藏
页码：192 / 193
页数：2
相关论文
共 22 条
  • [1] Microwave-promoted synthesis of β-hydroxy sulfides and β-hydroxy sulfoxides in water
    Pironti, V
    Colonna, S
    GREEN CHEMISTRY, 2005, 7 (01) : 43 - 45
  • [2] Rongalite® promoted highly regioselective synthesis of β-hydroxy sulfides by ring opening of epoxides with disulfides
    Guo, Wenxue
    Chen, Jiuxi
    Wu, Dengze
    Ding, Jinchang
    Chen, Fan
    Wu, Huayue
    TETRAHEDRON, 2009, 65 (27) : 5240 - 5243
  • [3] CsOH-promoted epoxide ring-opening with phosphines: mild and efficient synthesis of monohydroxyphosphines
    Fox, DL
    Robinson, AA
    Frank, JB
    Salvatore, RN
    TETRAHEDRON LETTERS, 2003, 44 (41) : 7579 - 7582
  • [4] A safe and scalable synthesis of 2-hydroxy-3-alkoxypropionates by epoxide ring opening
    Waring, Michael J.
    Bennett, Stuart N. L.
    Campbell, Leonie
    Hallam, Stephen
    Martin, Nathaniel G.
    Tickner, Christopher
    TETRAHEDRON LETTERS, 2015, 56 (34) : 4904 - 4907
  • [5] CSOH-promoted epoxide ring-opening with phosphines: Mild and efficient synthesis of monohydroxyphosphines.
    Robinson, AA
    Frank, B
    Fox, DL
    Salvatore, RN
    ABSTRACTS OF PAPERS OF THE AMERICAN CHEMICAL SOCIETY, 2003, 226 : U132 - U132
  • [6] An Efficient Microwave-Promoted Route to (Z)-Stilbenes from trans-Cinnamic Acids: Synthesis of Combretastatin A-4 and Analogues
    Bazin, Marc-Antoine
    Jouanne, Marie
    El-Kashef, Hussein
    Rault, Sylvain
    SYNLETT, 2009, (17) : 2789 - 2794
  • [7] AlEt3-promoted eliminative ring-opening of β-hydroxy epoxides:: highly stereoselective synthesis of terminal α-hydroxy olefins
    Wang, F
    Wang, SH
    Tu, YQ
    Ren, SK
    TETRAHEDRON-ASYMMETRY, 2003, 14 (15) : 2189 - 2193
  • [8] Erbium(III) Triflate is a Highly Efficient Catalyst for the Synthesis of β-Alkoxy Alcohols, 1,2-Diols and β-Hydroxy Sulfides by Ring Opening of Epoxides
    Dalpozzo, Renato
    Nardi, Monica
    Oliverio, Manuela
    Paonessa, Rosina
    Procopio, Antonio
    SYNTHESIS-STUTTGART, 2009, (20): : 3433 - 3438
  • [9] Tandem epoxide or aziridine ring opening by azide/copper catalyzed [3+2] cycloaddition:: Efficient synthesis of 1,2,3-triazolo β-hydroxy or β-tosylamino functionality motif
    Kumaraswamy, Gullapalli
    Ankamma, Kukkadapu
    Pitchaiah, Arigala
    JOURNAL OF ORGANIC CHEMISTRY, 2007, 72 (25): : 9822 - 9825
  • [10] Efficient solid-state microwave-promoted complexation of a mixed dioxa-diaza macrocycle with an alkali salt. Synthesis of a sodium ethyl 4-benzeneazophosphonate complex
    Tusek-Bozic, Ljerka
    Marotta, Ester
    Traldi, Pietro
    POLYHEDRON, 2007, 26 (08) : 1663 - 1668
123