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
相关论文
共 50 条
  • [41] Intramolecular 4+3 cycloadditions: Aspects of stereocontrol in the synthesis of cyclooctanoids.
    Harmata, M
    Rashatasakhon, P
    ABSTRACTS OF PAPERS OF THE AMERICAN CHEMICAL SOCIETY, 2000, 220 : U32 - U32
  • [42] Vinyl oxocarbenium ions in intermolecular [4+3] cycloaddition reactions
    Harmata, M
    Jones, DE
    JOURNAL OF ORGANIC CHEMISTRY, 1997, 62 (06): : 1578 - 1579
  • [43] Intramolecular 4+3 cycloadditions of oxyallyl zwitterions derived from the Nazarov cyclization
    Wang, Y
    West, FG
    ABSTRACTS OF PAPERS OF THE AMERICAN CHEMICAL SOCIETY, 1998, 216 : U479 - U479
  • [44] Regioselectivities of (4+3) Cycloadditions between Furans and Oxazolidinone-Substituted Oxyallyls
    Lohse, Andrew G.
    Krenske, Elizabeth H.
    Antoline, Jennifer E.
    Houk, K. N.
    Hsung, Richard P.
    ORGANIC LETTERS, 2010, 12 (23) : 5506 - 5509
  • [45] [4+3] cycloadditions of cyclic oxyallyls and cyclic 1,3-dienes
    Jin, Shu Juan
    Choi, Jong Ryoo
    Oh, Jonghoon
    Lee, Dngha
    Cha, Jin Kun
    Journal of the American Chemical Society, 1995, 117 (44):
  • [46] Asymmetric [4+3] cycloadditions from chiral alpha-chloro imines
    Kende, AS
    Huang, H
    TETRAHEDRON LETTERS, 1997, 38 (19) : 3353 - 3356
  • [47] Intramolecular 4+3 cycloadditions. Allylic sulfones as precursors to vinylthionium ions
    Harmata, M
    Kahraman, M
    TETRAHEDRON LETTERS, 1998, 39 (21) : 3421 - 3424
  • [48] Origin of Stereoselectivity in the (4+3) Cycloadditions of Chiral Alkoxy Siloxyallyl Cations with Furan
    Krenske, Elizabeth H.
    Houk, K. N.
    Harmata, Michael
    ORGANIC LETTERS, 2010, 12 (03) : 444 - 447
  • [49] Nazarov Reactions Intercepted by (4+3) Cycloadditions with Oxygen-Substituted Dienes
    LeFort, Francois M.
    Mishra, Vinayak
    Dexter, Graham D.
    Morgan, Timothy D. R.
    Burnell, D. Jean
    JOURNAL OF ORGANIC CHEMISTRY, 2015, 80 (11): : 5877 - 5886
  • [50] Diastereoselective [4+3] cycloadditions of enantiopure nitrogen-stabilized oxyallyl cations
    MaGee, David I.
    Godineau, Edouard
    Thornton, Paul D.
    Walters, Michael A.
    Sponholtz, Deborah J.
    EUROPEAN JOURNAL OF ORGANIC CHEMISTRY, 2006, 2006 (16) : 3667 - 3680
12345