Dual Catalysis in Enantioselective Oxidopyrylium-Based [5+2] Cycloadditions

被引：174
|
作者：
Burns, Noah Z. [1 ]
Witten, Michael R. [1 ]
Jacobsen, Eric N. [1 ]
机构：
[1] Harvard Univ, Dept Chem & Chem Biol, Cambridge, MA 02138 USA
来源：
JOURNAL OF THE AMERICAN CHEMICAL SOCIETY | 2011年 / 133卷 / 37期
关键词：
2-DIAZO-3,6-DIKETOESTER-DERIVED CARBONYL YLIDES; 1,3-DIPOLAR CYCLOADDITION; ALKENE CYCLOADDITIONS; TUMOR PROMOTERS; SELECTIVITY; DITERPENE; ADDITIONS; ACCESS; ROUTE;
D O I：
10.1021/ja206997e
中图分类号：
O6 [化学];
学科分类号：
0703 ;
摘要：
A new method for effecting catalytic enantioselective intramolecular [5 + 2] cycloadditions based on oxidopyrylium intermediates is reported. The dual catalyst system consists of a chiral primary aminothiourea and a second achiral thiourea. Experimental evidence points to a new type of cooperative catalysis with each species being necessary to generate a reactive pyrylium ion pair that undergoes subsequent cycloaddition with high enantioselectivity.
引用
收藏
页码：14578 / 14581
页数：4
相关论文
共 50 条
  • [31] Investigation of oxygen tethered pyrones toward [5+2] cycloadditions
    Mitchell, Timothy
    Goodell, John
    Bulandr, Jacob
    [J]. ABSTRACTS OF PAPERS OF THE AMERICAN CHEMICAL SOCIETY, 2018, 255
  • [32] Oxidopyrylium [5+2] cycloaddition chemistry: Historical perspective and recent advances (2008-2018)
    Bejcek, Lauren P.
    Murelli, Ryan P.
    [J]. TETRAHEDRON, 2018, 74 (21) : 2501 - 2521
  • [33] A practical approach to stereochemically defined tetrahydrofurans from [5+2] oxidopyrylium-alkene cycloadducts
    Yadav, Arun A.
    Sarang, Prajakta S.
    Trivedi, Girish K.
    Salunkhe, Manikrao M.
    [J]. SYNLETT, 2007, (06) : 989 - 991
  • [34] [3+2]-CYCLOADDITIONS AND [5+2]-CYCLOADDITIONS OF THE CYCLOHEPTA-2,4-DIENYL CATION
    HEILMANN, W
    KOSCHINSKY, R
    MAYR, H
    [J]. JOURNAL OF ORGANIC CHEMISTRY, 1987, 52 (10): : 1989 - 1993
  • [35] New catalysts for [5+2] cycloadditions of vinylcyclopropanes: Carbon-carbon bond formation in water and asymmetric catalysis.
    Wender, PA
    Love, JA
    Lim, JH
    [J]. ABSTRACTS OF PAPERS OF THE AMERICAN CHEMICAL SOCIETY, 2000, 219 : U134 - U134
  • [36] Catalytic regio- and stereoselective intermolecular [5+2] cycloaddition via conjugative activation of oxidopyrylium
    Zhang, Ling
    Shi, Qiu
    Cao, Tongxiang
    Zhu, Shifa
    [J]. CHEMICAL COMMUNICATIONS, 2020, 56 (66) : 9533 - 9536
  • [37] Iridium Catalyzed Carbocyclizations: Efficient (5+2) Cycloadditions of Vinylcyclopropanes and Alkynes
    Melcher, Michaela-Christina
    von Wachenfeldt, Henrik
    Sundin, Anders
    Strand, Daniel
    [J]. CHEMISTRY-A EUROPEAN JOURNAL, 2015, 21 (02) : 531 - 535
  • [38] Origins of the stereoselectivities of type II intramolecular 5+2 cycloadditions of oxidopyridiniums
    Patel, Ashay
    Houk, Kendall
    [J]. ABSTRACTS OF PAPERS OF THE AMERICAN CHEMICAL SOCIETY, 2015, 250
  • [39] Recent development on the [5+2] cycloadditions and their application in natural product synthesis
    Gao, Kai
    Zhang, Yong-Gang
    Wang, Zhiming
    Ding, Hanfeng
    [J]. CHEMICAL COMMUNICATIONS, 2019, 55 (13) : 1859 - 1878
  • [40] Iridium catalyzed carbocyclizations: Efficient (5+2) cycloadditions of vinylcyclopropanes and alkynes
    Melcher, Michaela-Christina
    Strand, Daniel
    [J]. ABSTRACTS OF PAPERS OF THE AMERICAN CHEMICAL SOCIETY, 2015, 250
12345