Intermolecular (4+3) cycloadditions of aziridinyl enolsilanes

被引：17
作者：
Lam, Sze Kui
Lam, Sarah
Wong, Wing-Tak
Chiu, Pauline [1 ]
机构：
[1] Univ Hong Kong, Dept Chem, Hong Kong, Hong Kong, Peoples R China
来源：
CHEMICAL COMMUNICATIONS | 2014年 / 50卷 / 14期
关键词：
OXYALLYL CATIONS; EPOXY ENOLSILANES;
D O I：
10.1039/c3cc48266a
中图分类号：
O6 [化学];
学科分类号：
0703 ;
摘要：
Upon activation by strong Bronsted acids, aziridinyl enolsilanes undergo (4+3) cycloadditions with dienes to afford aminoalkylated cycloheptenones as products. The use of a highly polar medium such as nitroalkane facilitates high cycloaddition yields of up to 99%. Optically pure aziridinyl enolsilanes react to yield (4+3) cycloadducts with up to 99% ee.
引用
收藏
页码：1738 / 1741
页数：4
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    Alonso, Isaac
    Faustino, Helio
    Lopez, Fernando
    Mascarenas, Jose L.
    [J]. ANGEWANDTE CHEMIE-INTERNATIONAL EDITION, 2011, 50 (48) : 11496 - 11500
  • [2] The cycloaddition strategy for the synthesis of natural products containing carbocyclic seven-membered rings
    Battiste, MA
    Pelphrey, PM
    Wrightthl, DL
    [J]. CHEMISTRY-A EUROPEAN JOURNAL, 2006, 12 (13) : 3438 - 3447
  • [3] Inter- and Intramolecular [4+3] Cycloadditions Using Epoxy Enol Silanes As Functionalized Oxyallyl Cation Precursors
    Chung, Wing Ki
    Lam, Sze Kui
    Lo, Brian
    Liu, Lok Lok
    Wong, Wing-Tak
    Chiu, Pauline
    [J]. JOURNAL OF THE AMERICAN CHEMICAL SOCIETY, 2009, 131 (13) : 4556 - +
  • [4] Regioselective reactions of 1-alkylidene-2-oxyallyl cations with furan: Control of [4+3] cycloaddition, [3+2] cycloaddition, and electrophilic substitution
    Fujita, Morifumi
    Oshima, Makoto
    Okuno, Sakuro
    Sugimura, Takashi
    Okuyama, Tadashi
    [J]. ORGANIC LETTERS, 2006, 8 (18) : 4113 - 4116
  • [5] Asymmetric organocatalysis of 4+3 cycloaddition reactions
    Harmata, M
    Ghosh, SK
    Hong, XC
    Wacharasindhu, S
    Kirchhoefer, P
    [J]. JOURNAL OF THE AMERICAN CHEMICAL SOCIETY, 2003, 125 (08) : 2058 - 2059
  • [6] The (4+3)-cycloaddition reaction: simple allylic cations as dienophiles
    Harmata, Michael
    [J]. CHEMICAL COMMUNICATIONS, 2010, 46 (47) : 8886 - 8903
  • [7] The (4+3)-cycloaddition reaction: heteroatom-substituted allylic cations as dienophiles
    Harmata, Michael
    [J]. CHEMICAL COMMUNICATIONS, 2010, 46 (47) : 8904 - 8922
  • [8] THE CYCLOADDITION OF ALLYL CATIONS TO 1,3-DIENES - GENERAL-METHOD FOR THE SYNTHESIS OF 7-MEMBERED CARBOCYCLES
    HOFFMANN, HMR
    [J]. ANGEWANDTE CHEMIE-INTERNATIONAL EDITION IN ENGLISH, 1984, 23 (01): : 1 - 19
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    Huang, J
    Hsung, RP
    [J]. JOURNAL OF THE AMERICAN CHEMICAL SOCIETY, 2005, 127 (01) : 50 - 51
  • [10] Enantiomerically Enriched (4+3) Cycloadducts from Optically Active Epoxy Enolsilanes
    Lam, Sarah
    Lo, Brian
    Wong, Wing-Tak
    Chiu, Pauline
    [J]. ASIAN JOURNAL OF ORGANIC CHEMISTRY, 2012, 1 (01) : 30 - 33
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