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  • Fukuyama Group - Group Meeting Problems 12/11/2010: T-Buome

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    The document summarizes reactions from 4 references: 1) Synthesis of a compound in 85% yield via two steps. 2) Synthesis of a compound in 50% yield via a palladium-catalyzed reaction. 3) Synthesis of a morpholine-containing compound in quantitative yield via two steps. 4) Synthesis of an ether compound in 70% yield via refluxing with TMSOTf and MeNO2.

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    The document summarizes reactions from 4 references: 1) Synthesis of a compound in 85% yield via two steps. 2) Synthesis of a compound in 50% yield via a palladium-catalyzed reaction. 3) Synthesis of a morpholine-containing compound in quantitative yield via two steps. 4) Synthesis of an ether compound in 70% yield via refluxing with TMSOTf and MeNO2.

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    1 views1 page

    Fukuyama Group - Group Meeting Problems 12/11/2010: T-Buome

    Uploaded by

    Anonymous rhUNqC1s0
    The document summarizes reactions from 4 references: 1) Synthesis of a compound in 85% yield via two steps. 2) Synthesis of a compound in 50% yield via a palladium-catalyzed reaction. 3) Synthesis of a morpholine-containing compound in quantitative yield via two steps. 4) Synthesis of an ether compound in 70% yield via refluxing with TMSOTf and MeNO2.

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    © All Rights Reserved
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    Fukuyama Group - Group Meeting Problems

    12/11/2010
    1
    1) h
    EtOH, rt, 85%

    O
    N

    2) TFA, rt, 80%

    N
    O

    N
    M. Ishikawa et al., Tetrahedron Lett., 11, 2329 (1970)

    OH

    Pd(dba)2
    Me3SiSnBu3
    toluene, 80 C
    50%

    Cl

    TiCl4

    LTMP

    CH2Cl2
    78 C

    t-BuOMe
    0 C to rt

    60%

    59 %
    theoretically

    2 eq.

    D. M. Hodgson et al., J. Am. Chem. Soc., 129, 4456 (2007)

    3
    morpholine (2 eq)
    Dy(OTf)3 (10 mol%)

    O
    O

    2) NaH, BnBr, DMF


    0 C to rt, 84%

    MS4A, MeCN, rt

    1) NaBH4, CeCl37H2O
    MeOH, 0 C, 95%

    quant

    Cl

    TiCl4 (10 mol%)


    i-Pr2NEt (1.5 eq)
    CH2Cl2

    OBn
    O

    O
    N

    N
    O

    72%
    R. A. Batey et al., Chem. Commun., 3759 (2007)

    OMe
    O
    MeO

    OMe O

    TMSOTf (1.2 eq)


    O

    Me

    MeNO2, reflux
    70%

    H
    MeO

    Me

    E. Fillion and D. Fishlock, J. Am. Chem. Soc., 127, 13144 (2005)

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