Copper(I) Hydride-Catalyzed Asymmetric Hydrosilylation of Heteroaromatic Ketones

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Abstract

In situ generation of CuH ligated by Takasago's new nonracemic ligand, DTBM-SEGPHOS, leads to an especially reactive reagent capable of effecting asymmetric hydrosilylation of heteroaromatic (H) ketones under very mild conditions. PMHS serves as an inexpensive source of hydride. Substrate-to-ligand ratios on the order of 2000:1 are employed.

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This article has been cited by 17 ACS Journal articles (5 most recent appear below).

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  CuH-Catalyzed Enantioselective 1,2-Reductions of α,β-Unsaturated Ketones

  Ralph Moser, Žarko V. Bošković, Christopher S. Crowe and Bruce H. Lipshutz
  Journal of the American Chemical Society2010 132 (23), 7852-7853

  • CuH-Catalyzed Enantioselective 1,2-Reductions of α,β-Unsaturated Ketones

    Ralph Moser, Žarko V. Bošković, Christopher S. Crowe and Bruce H. Lipshutz
    Journal of the American Chemical Society2010 132 (23), 7852-7853

    The first study on a general technology for arriving at valued nonracemic allylic alcohols using asymmetric ligand-accelerated catalysis by copper hydride is described.

    Abstract | Full Text HTML | Hi-Res PDF | PDF w/ Links
• 

  Efficient Chemoenzymatic Dynamic Kinetic Resolution of 1-Heteroaryl Ethanols

  Karl S. A. Vallin, David Wensbo Posaric, Zdenko Hameršak, Mats A. Svensson and Alexander B. E. Minidis
  The Journal of Organic Chemistry2009 74 (24), 9328-9336

  • Efficient Chemoenzymatic Dynamic Kinetic Resolution of 1-Heteroaryl Ethanols

    Karl S. A. Vallin, David Wensbo Posaric, Zdenko Hameršak, Mats A. Svensson and Alexander B. E. Minidis
    The Journal of Organic Chemistry2009 74 (24), 9328-9336

    The scope and limitation of the combined ruthenium-lipase induced dynamic kinetic resolution (DKR) through O-acetylation of racemic heteroaromatic secondary alcohols, i.e., 1-heteroaryl substituted ethanols, was investigated. After initial screening of ...

    Abstract | Full Text HTML | Hi-Res PDF | PDF w/ Links
• 

  Asymmetric Conjugate Reductions of Coumarins. A New Route to Tolterodine and Related Coumarin Derivatives

  Brian D. Gallagher, Benjamin R. Taft and Bruce H. Lipshutz
  Organic Letters2009 11 (23), 5374-5377

  • Asymmetric Conjugate Reductions of Coumarins. A New Route to Tolterodine and Related Coumarin Derivatives

    Brian D. Gallagher, Benjamin R. Taft and Bruce H. Lipshutz
    Organic Letters2009 11 (23), 5374-5377

    The combination of catalytic amounts of [(R)-DTBM-SEGPHOS]CuH in the presence of stoichiometric DEMS (diethoxymethylsilane) in toluene at room temperature leads to asymmetric reductions of 4-substituted coumarins. Several targets or their known ...

    Abstract | Full Text HTML | Hi-Res PDF | PDF w/ Links
• 

  Asymmetric Hydrosilylation of Ketones Catalyzed by Magnetically Recoverable and Reusable Copper Ferrite Nanoparticles

  M. Lakshmi Kantam, Jagjit Yadav, Soumi Laha, Pottabathula Srinivas, Bojja Sreedhar and F. Figueras
  The Journal of Organic Chemistry2009 74 (12), 4608-4611

  • Asymmetric Hydrosilylation of Ketones Catalyzed by Magnetically Recoverable and Reusable Copper Ferrite Nanoparticles

    M. Lakshmi Kantam, Jagjit Yadav, Soumi Laha, Pottabathula Srinivas, Bojja Sreedhar and F. Figueras
    The Journal of Organic Chemistry2009 74 (12), 4608-4611

    Herein we present magnetically recoverable and reusable copper ferrite nanoparticles for asymmetric hydrosilylation of several ketones. Up to 99% enantiometric excess was obtained at room temperature using polymethylhydrosiloxane as the stoichiometric ...

    Abstract | Full Text HTML | Hi-Res PDF | PDF w/ Links
• 

  Catalytic Hydrosilylation of the Carbonyl Functionality via a Transient Nickel Hydride Complex

  Ba L. Tran, Maren Pink and Daniel J. Mindiola
  Organometallics2009 28 (7), 2234-2243

  • Catalytic Hydrosilylation of the Carbonyl Functionality via a Transient Nickel Hydride Complex

    Ba L. Tran, Maren Pink and Daniel J. Mindiola
    Organometallics2009 28 (7), 2234-2243

    We report the catalytic hydrosilylation of carbonyl compounds utilizing the system of [(PNiPr3)Ni(μ2-Br)]2 (PNiPr3 = N-(2-(diisopropylphosphino)-4-methylphenyl)-2,4,6-triisopropylanilide), with KOtBu and Et3SiH. Shown in the scheme is the plausible ...

    Abstract | Full Text HTML | Hi-Res PDF | PDF w/ Links

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