One-pot enyne ring-closing metathesis-Diels-Alder reactions for the synthesis of polycyclic sulfamides

被引：7
|
作者：
Hill-Cousins, Joseph T. [1 ]
Salim, Sofia S. [1 ]
Bakar, Youssef M. [1 ]
Bellingham, Richard K. [2 ]
Light, Mark E. [1 ]
Brown, Richard C. D. [1 ]
机构：
[1] Univ Southampton, Dept Chem, Southampton SO17 1BJ, Hants, England
[2] GlaxoSmithKline, Dept Synthet Chem, Chem Dev, Tonbridge TN11 9AN, Kent, England
来源：
TETRAHEDRON | 2014年 / 70卷 / 23期
基金：
英国工程与自然科学研究理事会;
关键词：
Metathesis; Enyne; Sulfamide; Diels-Alder; One-pot; SOLID-PHASE SYNTHESIS; NATURAL-PRODUCTS; ACID; ISOMERIZATION; DERIVATIVES; STRATEGIES;
D O I：
10.1016/j.tet.2014.04.014
中图分类号：
O62 [有机化学];
学科分类号：
070303 ; 081704 ;
摘要：
Ring-closing metathesis (RCM) and sequential Yb(OTf)(3) promoted Diels-Alder reactions of sulfamide-linked enynes proceeded selectively in one-pot-to afford-a series of bicyclic and tricyclic sulfamides. Excellent levels of diastereoselectivity are observed for the cycloaddition step, with only the endo-adducts being isolated. The protocol was further extended to incorporate a one-pot RCM-cross metathesis (CM)-Diels-Alder sequence, permitting rapid access to high levels of molecular complexity from simple and easily accessible precursors. Crown Copyright (C) 2014 Published by Elsevier Ltd. All rights reserved.
引用
收藏
页码：3700 / 3706
页数：7
相关论文
共 50 条
  • [31] Synthesis of oxacyclic dienes via ring-closing enyne metathesis: difference in construction of eight-membered rings
    Zhang, Lin-Lin
    Zhang, Wen-Zhen
    Ren, Xiang
    Tan, Xin-Yan
    Lu, Xiao-Bing
    TETRAHEDRON LETTERS, 2012, 53 (26) : 3389 - 3392
  • [32] Synthesis of quinoline/oxindole appended phenylvinyl-2,5-dihydrofuran derivatives via ring-closing enyne metathesis
    George, Kevin
    Kannadasan, Sathananthan
    TETRAHEDRON, 2023, 142
  • [33] One-Pot Ring-Closing Metathesis/1,3-Dipolar Cycloaddition through Assisted Tandem Ruthenium Catalysis: Synthesis of a Dye with Isoindolo[2,1-a]quinoline Structure
    Arisawa, Mitsuhiro
    Fujii, Yuki
    Kato, Hiroshige
    Fukuda, Hayato
    Matsumoto, Takashi
    Ito, Mika
    Abe, Hiroshi
    Ito, Yoshihiro
    Shuto, Satoshi
    ANGEWANDTE CHEMIE-INTERNATIONAL EDITION, 2013, 52 (03) : 1003 - 1007
  • [34] Synthesis of New Allocolchicinoids with Seven- and Eight-Membered B-Rings by Enyne Ring-Closing Metathesis
    Boyer, Francois-Didier
    Hanna, Issam
    EUROPEAN JOURNAL OF ORGANIC CHEMISTRY, 2008, 2008 (29) : 4938 - 4948
  • [35] Synthesis of Bicyclic Thiazolidinethiones and Oxazolidinones by Water-Mediated Multicomponent Reactions (MCR) and Ring-Closing Metathesis (RCM)
    Stalling, Timo
    Saak, Wolfgang
    Martens, Juergen
    EUROPEAN JOURNAL OF ORGANIC CHEMISTRY, 2013, 2013 (35) : 8022 - 8032
  • [36] One-pot three-step thioconjugate addition-oxidation-Diels-Alder reactions of ethyl propiolate
    Downey, C. Wade
    Craciun, Smaranda
    Vivelo, Christina A.
    Neferu, Ana M.
    Mueller, Carly J.
    Corsi, Stephanie
    TETRAHEDRON LETTERS, 2012, 53 (43) : 5766 - 5768
  • [37] Diels-Alder reaction of methoxythiophenes: A new one-pot synthesis of dimethyl phthalates
    Corral, C
    Lissavetzky, J
    Manzanares, I
    SYNTHESIS-STUTTGART, 1997, (01): : 29 - &
  • [38] Synthesis of oxygen-containing medium and large rings using one-pot combinations of sequential alkene, enyne and alkyne metathesis reactions
    Groaz, Elisabetta
    Banti, Donatella
    North, Michael
    ADVANCED SYNTHESIS & CATALYSIS, 2007, 349 (1-2) : 142 - 146
  • [39] Substituent-controlled domino-Knoevenagel-hetero Diels-Alder reaction-a one-pot synthesis of polycyclic heterocycles
    Maiti, Sourav
    Panja, Suman Kalyan
    Bandyopadhyay, Chandrakanta
    TETRAHEDRON, 2010, 66 (38) : 7625 - 7632
  • [40] An enantio- and diastereoselective synthesis of fluorinated β-aminoalkyloxepine derivatives through Mannich and ring-closing metathesis reactions
    Fustero, Santos
    Esteban, Elisabet
    Sanz-Cervera, Juan F.
    Jimenez, Diego
    Mojarrad, Fatemeh
    SYNTHESIS-STUTTGART, 2006, (23): : 4087 - 4091
12345