Nickel(0) Triethyl Phosphite Complex-Catalyzed Allylic Substitution with Retention of Regio- and Stereochemistry

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Abstract

Nickel(0) triethyl phosphite complex-promoted reaction of allylic acetates with thiols produced allylic sulfides with retention of configuration without allylic rearrangement. A similar reaction of allylic acetates with alcohols and phenols also proceeded with retention of regio- and stereochemistry.

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This article has been cited by 4 ACS Journal articles (4 most recent appear below).

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  Iridium-Catalyzed Allylic Vinylation and Asymmetric Allylic Amination Reactions with o-Aminostyrenes

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  Journal of the American Chemical Society2011 133 (46), 19006-19014

  • Iridium-Catalyzed Allylic Vinylation and Asymmetric Allylic Amination Reactions with o-Aminostyrenes

    Ke-Yin Ye, Hu He, Wen-Bo Liu, Li-Xin Dai, Günter Helmchen, and Shu-Li You
    Journal of the American Chemical Society2011 133 (46), 19006-19014

    An Ir-catalyzed allylic vinylation reaction of allyl carbonates with o-aminostyrene derivatives has been realized, providing skipped (Z,E)-diene derivatives. With (E)-but-2-ene-1,4-diyl dimethyl dicarbonate as the substrate, an efficient enantioselective ...

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

  Oxazolidine Synthesis by Complementary Stereospecific and Stereoconvergent Methods

  Michael B. Shaghafi, Robin E. Grote, and Elizabeth R. Jarvo
  Organic Letters2011 13 (19), 5188-5191

  • Oxazolidine Synthesis by Complementary Stereospecific and Stereoconvergent Methods

    Michael B. Shaghafi, Robin E. Grote, and Elizabeth R. Jarvo
    Organic Letters2011 13 (19), 5188-5191

    Complementary stereospecific and stereoconvergent reactions for enantioselective synthesis of 1,3-oxazolidines are reported. In the presence of a rhodium catalyst, reaction of enantioenriched butadiene monoxide with aryl imines is stereospecific (99% ee). ...

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

  Transition-Metal-Catalyzed C−S, C−Se, and C−Te Bond Formation via Cross-Coupling and Atom-Economic Addition Reactions

  Irina P. Beletskaya and Valentine P. Ananikov
  Chemical Reviews2011 111 (3), 1596-1636

  • Transition-Metal-Catalyzed C−S, C−Se, and C−Te Bond Formation via Cross-Coupling and Atom-Economic Addition Reactions

    Irina P. Beletskaya and Valentine P. Ananikov
    Chemical Reviews2011 111 (3), 1596-1636
    Abstract | Full Text HTML | Hi-Res PDF | PDF w/ Links
• 

  Iridium-Catalyzed Enantioselective Allylic Substitution of O-Allyl Carbamothioates

  Qing-Long Xu, Wen-Bo Liu, Li-Xin Dai and Shu-Li You
  The Journal of Organic Chemistry2010 75 (13), 4615-4618

  • Iridium-Catalyzed Enantioselective Allylic Substitution of O-Allyl Carbamothioates

    Qing-Long Xu, Wen-Bo Liu, Li-Xin Dai and Shu-Li You
    The Journal of Organic Chemistry2010 75 (13), 4615-4618

    With an [Ir(COD)Cl]2/phosphoramidite ligand system, an allylic substitution of O-allyl carbamothioates was developed. The reaction proceeded in the favor of branched products with up to 93:7 branched-to-linear ratio, affording chiral S-allyl ...

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

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