Shengming Ma Chemistry Group Assignments

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  • Enantioselective Synthesis of Trisubstituted Allenyl–B(pin) Compounds by Phosphine–Cu-Catalyzed 1,3-Enyne Hydroboration. Insights Regarding Stereochemical Integrity of Cu–Allenyl Intermediates

    YoumingHuangJuandel PozoSebastianTorkerAmir H.Hoveyda

    Journal of the American Chemical Society2018140 (7), 2643-2655

    Abstract | Full Text HTML | PDF | PDF w/ Links

  • Catalytic One-Pot Synthesis of Trisubstituted Allenes from Terminal Alkynes and Ketones


    Organic Letters201719 (19), 5174-5177

    Abstract | Full Text HTML | PDF | PDF w/ Links

  • Unified Approach to Substituted Allenoates via Pd-Catalyzed β-Hydride Elimination of (E)-Enol Triflates

    MarieEl ArbaSara E.DibrellIan T.CrouchDoug E.Frantz

    Organic Letters201719 (19), 5446-5449

    Abstract | Full Text HTML | PDF | PDF w/ Links

  • Intramolecular Chirality Transfer [2 + 2] Cycloadditions of Allenoates and Alkenes

    YaoXuYoung J.HongDean J.TantilloM. KevinBrown

    Organic Letters201719 (14), 3703-3706

    Abstract | Full Text HTML | PDF | PDF w/ Links

  • Enantioselective Synthesis of Trisubstituted Allenes via Cu(I)-Catalyzed Coupling of Diazoalkanes with Terminal Alkynes


    Journal of the American Chemical Society2016138 (44), 14558-14561

    Abstract | Full Text HTML | PDF | PDF w/ Links

  • Proton Transfer Mechanism of Organocatalyzed Isomerization of Alkynoates into Allenoates: Enantioselectivity and Reversibility. A DFT Study


    ACS Catalysis20166 (5), 2988-2996

    Abstract | Full Text HTML | PDF | PDF w/ Links

  • Diastereoselective and Enantioselective Alleno-aldol Reaction of Allenoates with Isatins to Synthesis of Carbinol Allenoates Catalyzed by Gold


    ACS Catalysis20166 (4), 2482-2486

    Abstract | Full Text HTML | PDF | PDF w/ Links

  • Diastereoselective Synthesis of Tetrasubstituted Propargylamines via Hydroamination and Metalation of 1-Alkynes and Their Enantioselective Conversion to Trisubstituted Chiral Allenes

    MariappanPeriasamyPolimera ObulaReddyIddumSatyanarayanaLakavathuMohanAthukuriEdukondalu

    The Journal of Organic Chemistry201681 (3), 987-999

    Abstract | Full Text HTML | PDF | PDF w/ Links

  • Pd-Catalyzed Hydroborylation of Alkynes: A Ligand Controlled Regioselectivity Switch for the Synthesis of α- or β-Vinylboronates

    Devi PrasanOjhaKandikere RamaiahPrabhu

    Organic Letters201618 (3), 432-435

    Abstract | Full Text HTML | PDF | PDF w/ Links

  • Synthesis of Highly Substituted Racemic and Enantioenriched Allenylsilanes via Copper-Catalyzed Hydrosilylation of (Z)-2-Alken-4-ynoates with Silylboronate


  • Conspectus

    Modern synthetic chemists have looked for rapid and efficient ways to construct complex molecules while minimizing synthetic manipulation and maximizing atom-economy. Over the last few decades, researchers have made considerable progress toward these goals by taking full advantage of transition metal catalysis and the diverse reactivities of allenes, functional groups which include two cumulative carbon–carbon double bonds.

    This Account describes our efforts toward the development of Pd-catalyzed cyclization reactions of allenes in the presence of compounds that contain unsaturated carbon–carbon bonds such as alkenyl halides, simple alkenes, allenes, electron-deficient alkynes, or propargylic carbonates. First, we discuss the coupling-cyclization reactions of allenes bearing a nucleophilic functionality in the presence of alkenyl halides, simple alkenes, functionalized and nonfunctionalized allenes, or electron-deficient alkynes. These processes generally involve a Pd(II)-catalyzed sequence: cyclic nucleopalladation, insertion or nucleopalladation, and β-elimination, reductive elimination, cyclic allylation or protonation. We then focus on Pd(0)-catalyzed cyclization reactions of allenes in the presence of propargylic carbonates. In these transformations, oxidative addition of propargylic carbonates with Pd(0) affords allenylpalladium(II) species, which then react with allenes via insertion or nucleopalladation. These transformations provide easy access to a variety of synthetically versatile monocyclic, dumbbell-type bicyclic, and fused multicyclic compounds. We have also prepared a series of highly enantioenriched products using an axial-to-central chirality transfer strategy.

    A range of allenes are now readily available, including optically active ones with central and/or axial chirality. Expansion of these reactions to include other types of functionalized allenes, such as allenyl thiols, allenyl hydroxyl amines, and other structures with differing steric and electronic character, could allow access to cyclic skeletons that previously were difficult to prepare. We anticipate that other studies will continue to explore this promising area of synthetic organic chemistry.

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