An efficient approach to the synthesis of 3-vinylidene tetrahydropyrans via Prins-type cyclization

被引：15
|
作者：
Dziedzic, M [1 ]
Lipner, G [1 ]
Furman, B [1 ]
机构：
[1] Polish Acad Sci, Inst Organ Chem, PL-01224 Warsaw, Poland
来源：
TETRAHEDRON LETTERS | 2005年 / 46卷 / 40期
关键词：
propargylsilanes; tetrahydropyrans; Prins cyclization;
D O I：
10.1016/j.tetlet.2005.08.014
中图分类号：
O62 [有机化学];
学科分类号：
070303 ; 081704 ;
摘要：
Lewis acid-catalyzed intramolecular reactions of oxocarbenium ions with propargylsilanes are described. The results obtained indicate that trimethylsilyl trifluoromethanesulfonate (TMSOTf) efficiently catalyses cyclization leading to the corresponding 3-vinylidene tetrahydropyrans in high yield as single isomers. (c) 2005 Elsevier Ltd. All rights reserved.
引用
收藏
页码：6861 / 6863
页数：3
相关论文
共 50 条
  • [41] Iron(III)-Catalyzed Prins Cyclization towards the Synthesis of trans-Fused Bicyclic Tetrahydropyrans
    Perez, Sixto J.
    Miranda, Pedro O.
    Cruz, Daniel A.
    Fernandez, Israel
    Martin, Victor S.
    Padron, Juan I.
    SYNTHESIS-STUTTGART, 2015, 47 (12): : 1791 - 1798
  • [42] Synthesis of spiroketal fragment of ossamycin via Prins cyclization
    Yadav, J. S.
    Rahman, Md. Ataur
    Reddy, N. Mallikarjuna
    Prasad, A. R.
    TETRAHEDRON LETTERS, 2015, 56 (02) : 365 - 367
  • [43] Stereoselective Total Synthesis of Obolactone via Prins Cyclization
    Sabitha, Gowravaram
    Prasad, M. Nagendra
    Shankaraiah, K.
    Yadav, Jhillu S.
    SYNTHESIS-STUTTGART, 2010, (07): : 1171 - 1175
  • [44] Prins Cyclization in Ionic Liquid Hydrogen Fluoride Salts: Facile and Highly Efficient Synthesis of 4-Fluorinated Tetrahydropyrans, Thiacyclohexanes, and Piperidines
    Kishi, Yuichiro
    Inagi, Shinsuke
    Fuchigami, Toshio
    EUROPEAN JOURNAL OF ORGANIC CHEMISTRY, 2009, 2009 (01) : 103 - 109
  • [45] Diastereoselective Synthesis of Substituted Tetrahydropyrans by Copper(II)-Bisphosphine-Catalyzed Olefin Migration and Prins Cyclization
    Ghosh, Arun K.
    Kass, Jorden
    Nicponski, Daniel R.
    Keyes, Chad
    SYNTHESIS-STUTTGART, 2012, 44 (23): : 3579 - 3589
  • [46] Formal synthesis of (+)-SCH 351448: the Prins cyclization approach
    Chan, Kok-Ping
    Ling, Yvonne Hui
    Loh, Teck-Peng
    CHEMICAL COMMUNICATIONS, 2007, (09) : 939 - 941
  • [47] Synthesis of an austrodorane sesquiterpenoid core via a transannular Prins cyclization
    Clarke, Paul A.
    Winn, Joby
    TETRAHEDRON LETTERS, 2011, 52 (13) : 1469 - 1472
  • [48] The Stereoselective Total Synthesis of Aculeatin A and B via Prins Cyclization
    Yadav, J. S.
    Thrimurtulu, N.
    Venkatesh, M.
    Prasad, A. R.
    SYNTHESIS-STUTTGART, 2010, (03): : 431 - 436
  • [49] Stereoselective Total Synthesis of Rhoiptelol B via Prins Cyclization
    Yadav, Jhillu S.
    Rahman, Md Ataur
    Reddy, N. Mallikarjuna
    Prasad, Attaluri R.
    Al Ghamdi, Ahmad Al Khazim
    SYNLETT, 2014, 25 (05) : 661 - 664
  • [50] Stereoselective formal synthesis of crocacin C via prins cyclization
    Yadav, J. S.
    Reddy, M. Sridhar
    Rao, P. Purushothama
    Prasad, A. R.
    SYNLETT, 2007, (13) : 2049 - 2052
12345