Microwave enabled external carboxymethyl substituents in the ring-closing metathesis

被引:77
|
作者
Yang, CM [1 ]
Murray, WV [1 ]
Wilson, LJ [1 ]
机构
[1] Johnson & Johnson Pharmaceut & Dev LLC, Raritan, NJ 08869 USA
关键词
D O I
10.1016/S0040-4039(03)00083-2
中图分类号
O62 [有机化学];
学科分类号
070303 ; 081704 ;
摘要
The ring-closing metathesis of diolefin substrates containing an external carboxymethyl substituent is presented. The reaction is enabled through microwave irradiation allowing greatly enhanced yields and conversion rates. The reaction results in the formation of carboxymethyl substituted dihydropyrroles, dihydrofurans, and cyclopentenes. In certain cases, pyrroles are formed through further in situ oxidation. (C) 2003 Elsevier Science Ltd. All rights reserved.
引用
收藏
页码:1783 / 1786
页数:4
相关论文
共 50 条
  • [31] Enyne ring-closing metathesis on heteroaromatic cations
    Nunez, Ana
    Cuadro, Ana M.
    Alvarez-Builla, Julio
    Vaquero, Juan J.
    CHEMICAL COMMUNICATIONS, 2006, (25) : 2690 - 2692
  • [32] Ring-Closing Metathesis of Acrylates: A Comparative Study
    Schmidt, Bernd
    Geissler, Diana
    CHEMCATCHEM, 2010, 2 (04) : 423 - 429
  • [33] Ring-closing metathesis approach to the octalactins.
    Smith, TE
    Balskus, EP
    ABSTRACTS OF PAPERS OF THE AMERICAN CHEMICAL SOCIETY, 2002, 223 : B219 - B219
  • [34] Diastereoselective ring-closing metathesis in the synthesis of dihydropyrans
    Schmidt, B
    Wildemann, H
    JOURNAL OF ORGANIC CHEMISTRY, 2000, 65 (18): : 5817 - 5822
  • [35] Synthesis of the mycolactone core by ring-closing metathesis
    Alexander, Matthew D.
    Fontaine, Shaun D.
    La Clair, James J.
    DiPasquale, Antonio G.
    Rheingold, Arnold L.
    Burkart, Michael D.
    CHEMICAL COMMUNICATIONS, 2006, (44) : 4602 - 4604
  • [36] Low catalyst loading in ring-closing metathesis
    Kadyrov, Renat
    ABSTRACTS OF PAPERS OF THE AMERICAN CHEMICAL SOCIETY, 2012, 244
  • [37] Synthesis of bicyclic nucleosides by ring-closing metathesis
    Ravn, J
    Nielsen, P
    JOURNAL OF THE CHEMICAL SOCIETY-PERKIN TRANSACTIONS 1, 2001, (09): : 985 - 993
  • [38] Synthesis of cyclic peptidosulfonamides by ring-closing metathesis
    Brouwer, AJ
    Liskamp, RMJ
    JOURNAL OF ORGANIC CHEMISTRY, 2004, 69 (11): : 3662 - 3668
  • [39] Organoboronates as templates in ring-closing metathesis.
    Yu, HW
    Wang, BH
    ABSTRACTS OF PAPERS OF THE AMERICAN CHEMICAL SOCIETY, 2000, 220 : U108 - U108
  • [40] Olefin cross metathesis and ring-closing metathesis in polymer chemistry
    Sinclair, Fern
    Alkattan, Mohammed
    Prunet, Joelle
    Shaver, Michael P.
    POLYMER CHEMISTRY, 2017, 8 (22) : 3385 - 3398