High diastereoselective [4+2] annulation of β,γ-unsaturated α-keto esters and p-quinone methides: Approach to polysubstituted 4-aryl chromans and tetrahydroquinolines

被引：6
作者：
Si, Wen [1 ]
Xu, Fan [1 ]
Liu, Zhanxu [1 ]
Song, Ran [1 ]
Lv, Jian [1 ]
机构：
[1] Qingdao Univ Sci & Technol, Coll Chem & Mol Engn, State Key Lab Base Ecochem Cal Engn,MOE, Key Lab Opt Elect Sensing & Analyt Chem Life Sci, Qingdao 266042, Peoples R China
来源：
TETRAHEDRON LETTERS | 2020年 / 61卷 / 31期
关键词：
4-Aryl chromans; Tetrahydroquinolines; p-Quinone methides; beta; gamma-Unsaturated alpha-keto esters; Diastereoselective; DIELS-ALDER REACTION; DOMINO OXA-MICHAEL/1,6-ADDITION REACTIONS; BINARY-ACID CATALYSIS; BETA-ALKYNYL KETONES; DNA-POLYMERASE-BETA; ASYMMETRIC-SYNTHESIS; MICHAEL ADDITION; CYCLIZATION; CYCLOADDITION; (+)-MYRISTININ-A;
D O I：
10.1016/j.tetlet.2020.152171
中图分类号：
O62 [有机化学];
学科分类号：
070303 ; 081704 ;
摘要：
DBU-mediated [4 + 2] annulation of fi,y-unsaturated 1-keto esters and p-quinone methides has been developed. Under mild conditions, the reaction afforded polysubstituted 4-aryl chromans and tetrahydroquinolines as single diastereoisomer in high yields (up to 91% yield) at room temperature. (C) 2020 Elsevier Ltd. All rights reserved.
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页数：5
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  • [1] Dienamine-Mediated Inverse-Electron-Demand Hetero-Diels-Alder Reaction by Using an Enantioselective H-Bond-Directing Strategy
    Albrecht, Lukasz
    Dickmeiss, Gustav
    Weise, Christian F.
    Rodriguez-Escrich, Carles
    Jorgensen, Karl Anker
    [J]. ANGEWANDTE CHEMIE-INTERNATIONAL EDITION, 2012, 51 (52) : 13109 - 13113
  • [2] Total Synthesis of (±)-Pestalachloride C and (±)-Pestalachloride D through a Biomimetic Knoevenagel/Hetero-Diels-Alder Cascade
    Arredondo, Vanessa
    Roa, Daniel E.
    Yan, Songyuan
    Liu-Smith, Feng
    Van Vranken, David L.
    [J]. ORGANIC LETTERS, 2019, 21 (06) : 1755 - 1759
  • [3] Synthesis of Water-Soluble Blue-Emissive Tricyclic 2-Aminopyridinium Salts by Three-Component Coupling-(3+3)-Anellation
    Bakulina, Olga
    Merkt, Franziska K.
    Knedel, Tim-Oliver
    Janiak, Christoph
    Mueller, Thomas J. J.
    [J]. ANGEWANDTE CHEMIE-INTERNATIONAL EDITION, 2018, 57 (52) : 17240 - 17244
  • [4] Organocatalytic Functionalization of Carboxylic Acids: Isothiourea-Catalyzed Asymmetric Intra- and Intermolecular Michael Addition-Lactonizations
    Belmessieri, Dorine
    Morrill, Louis C.
    Simal, Carmen
    Slawin, Alexandra M. Z.
    Smith, Andrew D.
    [J]. JOURNAL OF THE AMERICAN CHEMICAL SOCIETY, 2011, 133 (08) : 2714 - 2720
  • [5] Catalytic, Asymmetric Michael Reactions of Cyclic Diketones with β,γ-Unsaturated α-Ketoesters
    Calter, Michael A.
    Wang, Jun
    [J]. ORGANIC LETTERS, 2009, 11 (10) : 2205 - 2208
  • [6] BrOnsted Acid Catalyzed Domino 1,6-Addition/Intramolecular Cyclization Reactions: Diastereoselective Synthesis of Dihydrocoumarin Frameworks
    Cao, Zheng
    Zhou, Gui-Xiang
    Ma, Chun
    Jiang, Kang
    Mei, Guang-Jian
    [J]. SYNTHESIS-STUTTGART, 2018, 50 (06): : 1307 - 1314
  • [7] DBU-Promoted Nucleophilic Activation of Carbonic Acid Diesters
    Carafa, Marianna
    Mesto, Ernesto
    Quaranta, Eugenio
    [J]. EUROPEAN JOURNAL OF ORGANIC CHEMISTRY, 2011, 2011 (13) : 2458 - 2465
  • [8] Silver/Scandium-Cocatalyzed Bicyclization of β-Alkynyl Ketones Leading to Benzo[c]xanthenes and Naphtho[1,2-b]benzofurans
    Chen, Ke
    Liu, Shuai
    Wang, Dan
    Hao, Wen-Juan
    Zhou, Peng
    Tu, Shu-Jiang
    Jiang, Bo
    [J]. JOURNAL OF ORGANIC CHEMISTRY, 2017, 82 (21) : 11524 - 11530
  • [9] Organocatalytic [4+2] cyclizations of para-quinone methide derivatives with isocyanates
    Cheng, Yu-Chun
    Wang, Cong-Shuai
    Li, Tian-Zhen
    Gao, Feng
    Jiao, Yinchun
    Shi, Feng
    [J]. ORGANIC & BIOMOLECULAR CHEMISTRY, 2019, 17 (27) : 6662 - 6670
  • [10] (+)-myristinins A and D from Knema elegans, which inhibit DNA polymerase β and cleave DNA
    Deng, JZ
    Starck, SR
    Li, SS
    Hecht, SM
    [J]. JOURNAL OF NATURAL PRODUCTS, 2005, 68 (11): : 1625 - 1628
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