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
  • [21] Ring-closing metathesis in carbohydrate annulation
    Holt, DJ
    Barker, WD
    Jenkins, PR
    Davies, DL
    Garratt, S
    Fawcett, J
    Russell, DR
    Ghosh, S
    ANGEWANDTE CHEMIE-INTERNATIONAL EDITION, 1998, 37 (23) : 3298 - 3300
  • [22] Quantitative ring-closing metathesis of polyolefins
    Coates, GW
    Grubbs, RH
    JOURNAL OF THE AMERICAN CHEMICAL SOCIETY, 1996, 118 (01) : 229 - 230
  • [23] Ring-closing metathesis and ring-closing metathesis-isomerisation approach to 1-phosphonylated 2-benzazocines
    Dieltiens, Nicolai
    Stevens, Christian V.
    Masschelein, Kurt
    Hennebel, Geert
    Van der Jeught, Sarah
    TETRAHEDRON, 2008, 64 (19) : 4295 - 4303
  • [24] Synthesis of spirocyclic thiazolidinediones using ring-closing metathesis and one-pot sequential ring-closing/cross metathesis
    Dhara, Kalyan
    Paladhi, Sushovan
    Midya, Ganesh Chandra
    Dash, Jyotirmayee
    ORGANIC & BIOMOLECULAR CHEMISTRY, 2011, 9 (10) : 3801 - 3807
  • [25] A ring-closing metathesis approach for the synthesis of (±)-pregabalin
    Vivek D. Bobade
    Pravin C. Mhaske
    Kamlesh S. Vadgaonkar
    Shivaji H. Shelke
    Monatshefte für Chemie - Chemical Monthly, 2012, 143 : 847 - 851
  • [26] β-, γ- and δ-lactams as conformational constraints in ring-closing metathesis
    Tarling, CA
    Holmes, AB
    Markwell, RE
    Pearson, ND
    JOURNAL OF THE CHEMICAL SOCIETY-PERKIN TRANSACTIONS 1, 1999, (12): : 1695 - 1701
  • [27] Investigation of the ring-closing metathesis of peptides in water
    Cochrane, Stephen A.
    Huang, Zedu
    Vederas, John C.
    ORGANIC & BIOMOLECULAR CHEMISTRY, 2013, 11 (04) : 630 - 639
  • [28] Synthesis of cyclic peptides by ring-closing metathesis
    Reichwein, JF
    Versluis, C
    Liskamp, RMJ
    JOURNAL OF ORGANIC CHEMISTRY, 2000, 65 (19): : 6187 - 6195
  • [29] Cross-metathesis and ring-closing metathesis of olefinic monosaccharides
    Postema, MHD
    Piper, JL
    TETRAHEDRON LETTERS, 2002, 43 (39) : 7095 - 7099
  • [30] Ring-closing metathesis approach toward phosphonosugars
    Stoianova, DS
    Hanson, PR
    PHOSPHORUS SULFUR AND SILICON AND THE RELATED ELEMENTS, 2002, 177 (8-9) : 1967 - 1968