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    Fukuyama Group - Group Meeting Problems 10/06/2012: J. Rodriguez Et Al., Org. Lett., 12, 4212 (2010)

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    The document summarizes four recent research articles. Article 1 describes a method to synthesize a cyclic boron compound using a borylation reaction. Article 2 details a two-step synthesis of a cyclic ether using BF3-mediated cyclization and TfOH-promoted rearrangement. Article 3 involves a rhodium-catalyzed cycloaddition to form a cyclic nitrile oxide. Article 4 reports a gold-catalyzed cycloisomerization to form a spirocyclic product using microwave irradiation.

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    Fukuyama Group - Group Meeting Problems 10/06/2012: J. Rodriguez Et Al., Org. Lett., 12, 4212 (2010)

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    Anonymous rhUNqC1s0
    18 views3 pages
    The document summarizes four recent research articles. Article 1 describes a method to synthesize a cyclic boron compound using a borylation reaction. Article 2 details a two-step synthesis of a cyclic ether using BF3-mediated cyclization and TfOH-promoted rearrangement. Article 3 involves a rhodium-catalyzed cycloaddition to form a cyclic nitrile oxide. Article 4 reports a gold-catalyzed cycloisomerization to form a spirocyclic product using microwave irradiation.

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    The document summarizes four recent research articles. Article 1 describes a method to synthesize a cyclic boron compound using a borylation reaction. Article 2 details a two-step synthesis of a cyclic ether using BF3-mediated cyclization and TfOH-promoted rearrangement. Article 3 involves a rhodium-catalyzed cycloaddition to form a cyclic nitrile oxide. Article 4 reports a gold-catalyzed cycloisomerization to form a spirocyclic product using microwave irradiation.

    Copyright:

    © All Rights Reserved
    Download as PDF, TXT or read online from Scribd
    Download as pdf or txt
    18 views3 pages

    Fukuyama Group - Group Meeting Problems 10/06/2012: J. Rodriguez Et Al., Org. Lett., 12, 4212 (2010)

    Uploaded by

    Anonymous rhUNqC1s0
    The document summarizes four recent research articles. Article 1 describes a method to synthesize a cyclic boron compound using a borylation reaction. Article 2 details a two-step synthesis of a cyclic ether using BF3-mediated cyclization and TfOH-promoted rearrangement. Article 3 involves a rhodium-catalyzed cycloaddition to form a cyclic nitrile oxide. Article 4 reports a gold-catalyzed cycloisomerization to form a spirocyclic product using microwave irradiation.

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    © All Rights Reserved
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    of 3

    Fukuyama Group - Group Meeting Problems

    10/06/2012
    1
    N2

    O Ph

    microwave

    + Ph

    + BnNH2

    toluene, 140 C

    NBn
    O

    73%

    J. Rodriguez et al., Org. Lett., 12, 4212 (2010)

    2
    1) PhI(OAc)2 (1.2 eq.)
    HFIP, 0 C

    OMe

    HO
    O Si O

    OH

    MeO

    H O
    OMe

    2) TBAF, THF, rt
    40% (2 steps)
    S. Canesi et al., J. Org. Chem., 77, 7588 (2012)

    3
    p-TolSO2Na

    O
    TBS

    DMF, rt
    80%

    PhCH2Br

    TBAF

    NaHMDS, THF
    80 to 60 C

    THF
    80 to 70 C

    93%

    86%

    Ph

    K. Takeda et al., Org. Lett., 6, 4849 (2004)

    4
    MeO OTES

    PhCH2N3, BF3OEt2

    Rh2(OAc)4

    78 C to rt
    CH2Cl2

    CH2Cl2, 0 C to rt

    O
    N
    Ph

    90%

    47%

    J. Aube et al., Org. Lett., 2, 1657 (2000)

    Fukuyama Group - Group Meeting Problems


    10/13/2012
    (pin)BB(pin) (3 eq)
    Cu(OAc)2 (2 mol%)
    P(t-Bu)3 (7 mol%)

    1
    MeO

    toluene, 80 C

    OMe

    62%

    C28H52O8B4

    1H

    NMR (CDCl)3
    1.12 (s, 24 H)
    1.26 (s, 24 H)
    1.85 (s, 4 H)

    toluene, 100 C

    Ph
    OH

    OH

    PhCHO (3 eq)

    Ph

    Ph

    86%

    H. Yoshida et al., Angew. Chem. Int. Ed., 51, 235 (2012)


    T. Hiyama et al., Chem. Asian. J., 2, 1142 (2007)

    1) MeO
    Li

    Et

    t-BuO

    OMe

    THF, 78 C
    52%
    2) toluene, reflux;
    Ag2O, K2CO3, rt
    92%
    3) TFA, toluene, 0 C
    quant.

    H2O2, Na2CO3
    dioxane-H2O
    60 C;
    HCl aq.
    H2SO3 aq.
    0 C;

    NaOH
    CuSO4

    The intermediate
    contains
    5-membered ring. H2O, 70C

    O
    HO

    OMe

    Me
    O

    72%

    OMe

    H. W. Moore et al., J. Org. Chem., 60, 461 (1995)

    3
    Me
    N
    Ph

    COCF3
    O

    Me3S I, n-BuLi
    THF, 20 C to rt;
    AcOH, 80 C

    MeS
    Ph

    70% (2 steps)

    CF3
    N
    Me

    M. Kawase et al., Tetrahedron Lett., 53, 2782 (2012)

    4
    O

    1) MeO
    Cl
    Et3N, CH2Cl2, rt
    2) p-TsOHH2O
    THF-H2O, reflux

    3) NaIO4, NaHCO3 aq
    CH2Cl2, rt
    53% (3 steps)

    Br

    Monocyclic
    Compound

    1) Me
    In (powder)
    THF-NH4Cl aq, 0 C
    77%
    2) MsCl, Et3N
    hydroquinone
    toluene
    190 C (sealed tube)
    47%

    OMs
    Me
    H H

    MeO
    N

    B. Alcaide et al., Eur. J. Org. Chem., 98 (2005)

    Fukuyama Group - Group Meeting Problems


    10/31/2012
    1

    SPh2BF4

    N3

    KOH

    TiCl4

    DMSO
    0 C to rt

    CH2Cl2
    78 C to rt
    78% (2 steps)
    S. Baskaran et al., Chem. Commun., 48, 5778 (2012)

    2
    Me

    1) BF3OEt2
    CDCl3, rt
    quant.

    O
    Ph
    Ph

    O
    O

    2) TfOH (20 eq.)


    CDCl3, 30 C
    98%

    Me

    Ph

    Me

    Me

    T. Oshima et al., Eur. J. Org. Chem., 3917 (2012)

    3
    TMS

    O
    N2

    Rh2(esp)2 (0.5 mol%)

    TBAF

    CH2Cl2, rt

    THF, 45 C

    71%

    63%

    O
    O

    J. A. May et al., J. Am. Chem. Soc., 134, 17877 (2012)

    4
    Ph
    OMe
    (OC)5Cr

    Ph

    n-BuLi, THF, 78 C;
    TMSOTf;
    , CH3CN
    73%

    spiro
    compound

    [(JohnPhos)Au(CH3CN)][SbF6]
    (5 mol%)

    Ph

    DCE, 100 C, W
    Ph
    41%

    J. Barluenga et al., Angew. Chem., 124, 10523 (2012)

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