Lewis acid catalyzed regioselective ring opening of azetidines with alcohols and thiols

被引：26
|
作者：
Dwivedi, Sandeep K. [1 ]
Gandhi, Shikha [1 ]
Rastogi, Narnrata [1 ]
Singh, Vinod K. [1 ]
机构：
[1] Indian Inst Technol, Dept Chem, Kanpur 208016, Uttar Pradesh, India
来源：
TETRAHEDRON LETTERS | 2007年 / 48卷 / 31期
关键词：
D O I：
10.1016/j.tetlet.2007.06.033
中图分类号：
O62 [有机化学];
学科分类号：
070303 ; 081704 ;
摘要：
An efficient synthesis of amino ethers and amino thioethers has been achieved via the ring cleavage of N-tosylazetidines with alcohols or thiols. The reactions were studied in the presence of various Lewis acids and BF3 center dot OEt2 was found to be the most efficient. The products were obtained in modest to good yields under very mild conditions in 5-15 min. (c) 2007 Elsevier Ltd. All rights reserved.
引用
收藏
页码：5375 / 5377
页数：3
相关论文
共 50 条
  • [21] Efficient synthesis of β-amino alcohols catalyzed by niobium pentachloride:: Regioselective ring opening of epoxides with aromatic amines
    Narsaiah, A. Venkat
    Sreenu, D.
    Nagaiah, K.
    SYNTHETIC COMMUNICATIONS, 2006, 36 (21) : 3183 - 3189
  • [22] Lewis Acid Catalyzed Regioselective Hydroheteroarylation of Pentafulvenes
    Chand, S. Sarath
    Gopalan, Greeshma
    Santhini, P. V.
    Preethanuj, P.
    John, Jubi
    Harakat, Dominique
    Jaroschik, Florian
    Radhakrishnan, K. V.
    ORGANIC LETTERS, 2016, 18 (05) : 964 - 967
  • [23] Borinic Acid-Catalyzed Regioselective Ring-Opening of 3,4-and 2,3-Epoxy Alcohols with Halides
    Wang, Grace
    Taylor, Mark S.
    ADVANCED SYNTHESIS & CATALYSIS, 2020, 362 (02) : 398 - 403
  • [24] Meso-tetraarylporphyrin catalyzed highly regioselective ring opening of epoxides with acetic acid
    Zakavi, Saeed
    Karimipour, Gholam Reza
    Gharab, Nasrin Gholami
    CATALYSIS COMMUNICATIONS, 2009, 10 (04) : 388 - 390
  • [25] Efficient and Regioselective Ring-opening of Epoxides with Carboxylic Acid Catalyzed by Graphite Oxide
    Mirza-Aghayan, Maryam
    Tavana, Mahdieh Molaee
    Niazi, Elaheh Golam Alipour
    Boukherroub, Rabah
    LETTERS IN ORGANIC CHEMISTRY, 2020, 17 (07) : 532 - 538
  • [26] Silica sulfuric acid; An efficient and reusable catalyst for regioselective ring opening of epoxides by alcohols and water
    Salehi, P
    Dabiri, M
    Zolfigol, MA
    Fard, MAB
    PHOSPHORUS SULFUR AND SILICON AND THE RELATED ELEMENTS, 2004, 179 (06) : 1113 - 1121
  • [27] Acylation of alcohols, thiols and amines with carboxylic acids catalyzed by yttria-zirconia-based Lewis acid
    Kumar, P
    Pandey, RK
    Bodas, MS
    Dagade, SP
    Dongare, MK
    Ramaswamy, AV
    JOURNAL OF MOLECULAR CATALYSIS A-CHEMICAL, 2002, 181 (1-2) : 207 - 213
  • [28] Efficient and regioselective ring-opening of arylaziridines with alcohols, thiols, amines and N-heteroaromatic compounds using sulphated zirconia
    Llaveria, Josep
    Espinoza, Araceli
    Negron, Guillermo
    Isabel Matheu, M.
    Castillon, Sergio
    TETRAHEDRON LETTERS, 2012, 53 (20) : 2525 - 2529
  • [29] Highly Regioselective Ring Opening of Epoxides with Thiols Catalyzed by SbCl3 Under Solvent-Free Conditions
    Ghazanfari, Dadkhoda
    Hashemi, Mohammed M.
    Akhgar, Mohammad Reza
    Foroughi, Mohammad Mehdi
    Najafi-Zadeh, Fariba
    PHOSPHORUS SULFUR AND SILICON AND THE RELATED ELEMENTS, 2008, 183 (12) : 3018 - 3022
  • [30] Synthesis of amino thiols and isocysteines via regioselective ring opening of sulfamidates with tetrathiomolybdate
    Baig, R. B. Nasir
    Kumar, N. Y. Phani
    Mannuthodikayil, Jamsad
    Chandrasekaran, Srinivasan
    TETRAHEDRON, 2011, 67 (17) : 3111 - 3118
12345