Enantioselective Haloetherification by Asymmetric Opening of meso-Halonium Ions

被引:151
作者
Hennecke, Ulrich [1 ]
Mueller, Christian H. [1 ]
Froehlich, Roland [1 ]
机构
[1] Univ Munster, Inst Organ Chem, D-48149 Munster, Germany
关键词
BRONSTED ACID; HALOCYCLIZATION; BROMOLACTONIZATION; CATALYSIS; METAL; IODOCYCLIZATION; THIIRANIUM; COMPLEXES; BROMONIUM; SALTS;
D O I
10.1021/ol1028805
中图分类号
O62 [有机化学];
学科分类号
070303 ; 081704 ;
摘要
A new approach to enantioselective haloetherification reactions via desymmetrization of in situ-generated meso-halonium ions is described. The combination of N-haloamides as a halogen source and sodium salts of chiral phosphoric acids as catalysts can be used for the cyclization of symmetrical ene-diol substrates, yielding the haloetherification products under practical conditions in enantioenriched form.
引用
收藏
页码:860 / 863
页数:4
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共 46 条
  • [31] Br+ and I+ transfer from the halonium ions of adamantylideneadamantane to acceptor olefins. Halocyclization of 1,omega-alkenols and alkenoic acids proceeds via reversibly formed intermediates
    Neverov, AA
    Brown, RS
    [J]. JOURNAL OF ORGANIC CHEMISTRY, 1996, 61 (03) : 962 - 968
  • [32] Enantioselective Iodolactonizations of 4-Pentenoic Acid Derivatives Mediated by Chiral Salen-Co(II) Complex
    Ning, Zhaolun
    Jin, Rizhe
    Ding, Jinying
    Gao, Lianxun
    [J]. SYNLETT, 2009, (14) : 2291 - 2294
  • [33] Enantioselective pictet-spengler-type cyclizations of hydroxylactams: H-bond donor catalysis by anion binding
    Raheem, Izzat T.
    Thiara, Parvinder S.
    Peterson, Emily A.
    Jacobsen, Eric N.
    [J]. JOURNAL OF THE AMERICAN CHEMICAL SOCIETY, 2007, 129 (44) : 13404 - +
  • [34] Bronsted acid-catalyzed desymmetrization of meso-aziridines
    Rowland, Emily B.
    Rowland, Gerald B.
    Rivera-Otero, Edwin
    Antilla, Jon C.
    [J]. JOURNAL OF THE AMERICAN CHEMICAL SOCIETY, 2007, 129 (40) : 12084 - +
  • [35] Bronsted acid-catalyzed imine amidation
    Rowland, GB
    Zhang, HL
    Rowland, EB
    Chennamadhavuni, S
    Wang, Y
    Antilla, JC
    [J]. JOURNAL OF THE AMERICAN CHEMICAL SOCIETY, 2005, 127 (45) : 15696 - 15697
  • [36] Dual catalysis: A combined enantioselective bronsted acid and metal-catalyzed reaction-metal catalysis with chiral counterions
    Rueping, Magnus
    Antonchick, Andrey R.
    Brinkmann, Claus
    [J]. ANGEWANDTE CHEMIE-INTERNATIONAL EDITION, 2007, 46 (36) : 6903 - 6906
  • [37] Unifying Metal and Bronsted Acid Catalysis-Concepts, Mechanisms, and Classifications
    Rueping, Magnus
    Koenigs, Rene M.
    Atodiresei, Iuliana
    [J]. CHEMISTRY-A EUROPEAN JOURNAL, 2010, 16 (31) : 9350 - 9365
  • [38] Enantioselective halocyclization of polyprenoids induced by nucleophilic phosphoramidites
    Sakakura, Akira
    Ukai, Atsushi
    Ishihara, Kazuaki
    [J]. NATURE, 2007, 445 (7130) : 900 - 903
  • [39] Facile and Efficient Enantioselective Strecker Reaction of Ketimines by Chiral Sodium Phosphate
    Shen, Ke
    Liu, Xiaohua
    Cai, Yunfei
    Lin, Lili
    Feng, Xiaoming
    [J]. CHEMISTRY-A EUROPEAN JOURNAL, 2009, 15 (24) : 6008 - 6014
  • [40] Enantioselective organocatalytic reductive amination
    Storer, RI
    Carrera, DE
    Ni, Y
    MacMillan, DWC
    [J]. JOURNAL OF THE AMERICAN CHEMICAL SOCIETY, 2006, 128 (01) : 84 - 86