Allylmalonate as an Activator Subunit for the Initiation of Relay Ring-Closing Metathesis Reactions

被引:8
作者
Hoye, Thomas R. [1 ]
Jeon, Junha [1 ]
Tennakoon, Manomi A. [1 ]
机构
[1] Univ Minnesota, Dept Chem, Minneapolis, MN 55455 USA
基金
美国国家卫生研究院;
关键词
cyclization; metathesis; reaction mechanisms; ruthenium; CATALYSTS; EFFICIENT; INSIGHTS; STRATEGY; ANALOG;
D O I
10.1002/anie.201005044
中图分类号
O6 [化学];
学科分类号
0703 ;
摘要
Passing the baton: The relay ring-closing metathesis (RRCM) reaction of complex polyenes 1 has been studied. Several relay subunits (T) were examined and many did not sufficiently activate the RRCM. An allylmalonate-containing relay subunit solved this problem, and efficiently lead to the diene 2. TIPS=triisopropylsilyl. © 2011 WILEY-VCH Verlag GmbH & Co. KGaA, Weinheim.
引用
收藏
页码:2141 / 2143
页数:3
相关论文
共 50 条
  • [31] Kinetically E-selective macrocyclic ring-closing metathesis
    Shen, Xiao
    Nguyen, Thach T.
    Koh, Ming Joo
    Xu, Dongmin
    Speed, Alexander W. H.
    Schrock, Richard R.
    Hoveyda, Amir H.
    NATURE, 2017, 541 (7637) : 380 - +
  • [32] Synthesis of novel unsaturated bicyclic lactams by ring-closing metathesis
    Grossmith, CE
    Senia, F
    Wagner, J
    SYNLETT, 1999, (10) : 1660 - 1662
  • [33] The Pivotal Role of Symmetry in the Ruthenium-Catalyzed Ring-Closing Metathesis of Olefins
    Costabile, Chiara
    Mariconda, Annaluisa
    Cavallo, Luigi
    Longo, Pasquale
    Bertolasi, Valerio
    Ragone, Francesco
    Grisi, Fabia
    CHEMISTRY-A EUROPEAN JOURNAL, 2011, 17 (31) : 8618 - 8629
  • [34] Total Synthesis of the Terpenoid Buddledone A: 11-Membered Ring-Closing Metathesis
    Cai, Zhengxin
    Yongpruksa, Nattawut
    Harmata, Michael
    ORGANIC LETTERS, 2012, 14 (07) : 1661 - 1663
  • [35] Ring-closing metathesis in the synthesis of biologically active peptidomimetics of apicidin A
    Deshmukh, Prashant H.
    Schulz-Fademrecht, Carsten
    Procopiou, Panayiotis A.
    Vigushin, David A.
    Coombes, R. Charles
    Barrett, Anthony G. M.
    ADVANCED SYNTHESIS & CATALYSIS, 2007, 349 (1-2) : 175 - 183
  • [36] Effects of substituents on the multiple bonds on ring-closing metathesis of enynes
    Kitamura, T
    Sato, Y
    Mori, M
    ADVANCED SYNTHESIS & CATALYSIS, 2002, 344 (6-7) : 678 - 693
  • [37] Synthetic Approaches to Crinipellin Based Tetraquinanes via Ring-Rearrangement Metathesis and Ring-Closing Metathesis
    Kotha, Sambasivarao
    Keesari, Ramakrishna Reddy
    ASIAN JOURNAL OF ORGANIC CHEMISTRY, 2021, 10 (12) : 3456 - 3471
  • [38] Synthesis of a Ribose-Incorporating Medium Ring Scaffold via a Challenging Ring-Closing Metathesis Reaction
    Rankin, Stuart S.
    Caldwell, John J.
    Cronin, Nora B.
    van Montfort, Rob L. M.
    Collins, Ian
    EUROPEAN JOURNAL OF ORGANIC CHEMISTRY, 2016, 2016 (26) : 4496 - 4507
  • [39] Ring-closing metathesis as a basis for the construction of aromatic compounds
    Donohoe, TJ
    Orr, AJ
    Bingham, M
    ANGEWANDTE CHEMIE-INTERNATIONAL EDITION, 2006, 45 (17) : 2664 - 2670
  • [40] Enantioselective Synthesis of (+)-Isolysergol via Ring-Closing Metathesis
    Deck, Jason A.
    Martin, Stephen F.
    ORGANIC LETTERS, 2010, 12 (11) : 2610 - 2613