Diastereoselective Synthesis of Arylglycine Derivatives by Cationic Palladium(II)-Catalyzed Addition of Arylboronic Acids to N-tert-Butanesulfinyl Imino Esters

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Abstract

A cationic palladium-complex-catalyzed addition of arylboronic acids to N-tert-butanesulfinyl iminoacetates to yield the optically active arylglycine derivatives with moderate to good yield and high diastereoselectivity was developed. This reaction provides a convenient and efficient method for the synthesis of arylglycine derivatives.

Citing Articles

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This article has been cited by 13 ACS Journal articles (5 most recent appear below).

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  Copper-Catalyzed Petasis-Type Reaction: A General Route to α-Substituted Amides From Imines, Acid Chlorides, and Organoboron Reagents

  Marie S. T. Morin, Yingdong Lu, Daniel A. Black, and Bruce A. Arndtsen
  The Journal of Organic Chemistry2012 Article ASAP

  • Copper-Catalyzed Petasis-Type Reaction: A General Route to α-Substituted Amides From Imines, Acid Chlorides, and Organoboron Reagents

    Marie S. T. Morin, Yingdong Lu, Daniel A. Black, and Bruce A. Arndtsen
    The Journal of Organic Chemistry2012 Article ASAP

    A copper-catalyzed Petasis-type reaction of imines, acid chlorides, and organoboranes to form α-substituted amides is described. This reaction does not require the use of activated imines or the transfer of special units from the organoboranes and ...

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

  Cationic Palladium-Catalyzed [5 + 2] Annulation of 2-Acylmethoxyarylboronic Acids and Allenoates: Synthesis of 1-Benzoxepine Derivatives

  Xufen Yu and Xiyan Lu
  The Journal of Organic Chemistry2011 Article ASAP

  • Cationic Palladium-Catalyzed [5 + 2] Annulation of 2-Acylmethoxyarylboronic Acids and Allenoates: Synthesis of 1-Benzoxepine Derivatives

    Xufen Yu and Xiyan Lu
    The Journal of Organic Chemistry2011 Article ASAP

    The 1-benzoxepine derivatives were synthesized conveniently by cationic palladium-catalyzed [5 + 2] annulation reaction of 2-acylmethoxyarylboronic acids with allenoates in high yields. This annulation involves the intramolecular nucleophilic addition to ...

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

  Asymmetric Strecker Synthesis of α-Arylglycines

  Yolanda Pérez-Fuertes, James E. Taylor, David A. Tickell, Mary F. Mahon, Steven D. Bull, and Tony D. James
  The Journal of Organic Chemistry2011 Article ASAP

  • Asymmetric Strecker Synthesis of α-Arylglycines

    Yolanda Pérez-Fuertes, James E. Taylor, David A. Tickell, Mary F. Mahon, Steven D. Bull, and Tony D. James
    The Journal of Organic Chemistry2011 Article ASAP

    A practically simple three-component Strecker reaction for the asymmetric synthesis of enantiopure α-arylglycines has been developed. Addition of a range of aryl-aldehydes to a solution of sodium cyanide and (S)-1-(4-methoxyphenyl)ethylamine affords ...

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

  Comparison of Imine to Olefin Insertion Reactions: Generation of Five- and Six-Membered Lactams via a Nickel-Mediated CO, Olefin, CO, Imine Insertion Cascade

  Jason L. Davis and Bruce A. Arndtsen
  Organometallics2011 30 (7), 1896-1901

  • Comparison of Imine to Olefin Insertion Reactions: Generation of Five- and Six-Membered Lactams via a Nickel-Mediated CO, Olefin, CO, Imine Insertion Cascade

    Jason L. Davis and Bruce A. Arndtsen
    Organometallics2011 30 (7), 1896-1901

    Cationic nickel complexes of the form L2Ni(CH3)(RN═C(H)R)+ (L2 = bidentate nitrogen donor) have been probed for their ability to mediate olefin and imine migratory insertion reactions. While these complexes do not undergo alkene insertion into the nickel−...

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

  Transmetalation of Unsaturated Carbon Nucleophiles from Boron-Containing Species to the Mid to Late d-Block Metals of Relevance to Catalytic C−X Coupling Reactions (X = C, F, N, O, Pb, S, Se, Te)

  David V. Partyka
  Chemical Reviews2011 111 (3), 1529-1595

  • Transmetalation of Unsaturated Carbon Nucleophiles from Boron-Containing Species to the Mid to Late d-Block Metals of Relevance to Catalytic C−X Coupling Reactions (X = C, F, N, O, Pb, S, Se, Te)

    David V. Partyka
    Chemical Reviews2011 111 (3), 1529-1595
    Abstract | Full Text HTML | Hi-Res PDF | PDF w/ Links

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