Copper-Catalyzed Asymmetric N−H Insertion Reactions:  Couplings of Diazo Compounds with Carbamates to Generate α-Amino Acids

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Abstract

A Cu/chiral bipyridine catalyst has been developed for the asymmetric insertion of α-diazocarbonyl compounds into the N−H bonds of carbamates to generate an array of easily deprotected arylglycines in good ee. With respect to the reaction partners, as well as the ligand, this process complements the only other report of highly enantioselective N−H insertion reactions.

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

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  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 76 (15), 6038-6047

  • 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 76 (15), 6038-6047

    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
• 

  Diastereoselectively Switchable Enantioselective Trapping of Carbamate Ammonium Ylides with Imines

  Jun Jiang, Hua-Dong Xu, Jian-Bei Xi, Bai-Yan Ren, Feng-Ping Lv, Xin Guo, Li-Qin Jiang, Zhi-Yong Zhang, and Wen-Hao Hu
  Journal of the American Chemical Society2011 133 (22), 8428-8431

  • Diastereoselectively Switchable Enantioselective Trapping of Carbamate Ammonium Ylides with Imines

    Jun Jiang, Hua-Dong Xu, Jian-Bei Xi, Bai-Yan Ren, Feng-Ping Lv, Xin Guo, Li-Qin Jiang, Zhi-Yong Zhang, and Wen-Hao Hu
    Journal of the American Chemical Society2011 133 (22), 8428-8431

    The diastereoselectively switchable enantioselective trapping of protic carbamate ammonium ylides with imines is reported. The intriguing Rh2(OAc)4 and chiral Brønsted acid cocatalyzed three-component Mannich-type reaction of a diazo compound, a carbamate,...

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

  CpRu-Catalyzed O−H Insertion and Condensation Reactions of α-Diazocarbonyl Compounds

  Martina Austeri, Diane Rix, Walid Zeghida, and Jérôme Lacour
  Organic Letters2011 13 (6), 1394-1397

  • CpRu-Catalyzed O−H Insertion and Condensation Reactions of α-Diazocarbonyl Compounds

    Martina Austeri, Diane Rix, Walid Zeghida, and Jérôme Lacour
    Organic Letters2011 13 (6), 1394-1397

    [CpRu(CH3CN)3][PF6] and diimine ligands catalyze together the decomposition of α-diazocarbonyl compounds leading to O−H insertion and condensation reactions. In comparison with Rh(II) and Cu(I) complexes, the CpRu catalysts produce rapid and often more ...

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

  Comparison of 2,2′-Bipyridine and 2,2′-Bipyridyl-N,N′-dioxide as Ligands in Zinc Complexes

  Lucie Ducháčková, Vincent Steinmetz, Joël Lemaire, and Jana Roithová
  Inorganic Chemistry2010 49 (19), 8897-8903

  • Comparison of 2,2′-Bipyridine and 2,2′-Bipyridyl-N,N′-dioxide as Ligands in Zinc Complexes

    Lucie Ducháčková, Vincent Steinmetz, Joël Lemaire, and Jana Roithová
    Inorganic Chemistry2010 49 (19), 8897-8903

    The complexation abilities of 2,2′-bipyridine (bipy) and 2,2′-bipyridyl-N,N′-dioxide (bipydiox) toward zinc(II) and the influence of these ligands on the properties and reactivities of the investigated complexes are compared by means of mass spectrometry, ...

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

  Vinylogous Aldol Products from Chiral Crotylsilanes Obtained by Enantioselective Rh(II) and Cu(I) Carbenoid Si−H Insertion

  Jie Wu, Yu Chen and James S. Panek
  Organic Letters2010 12 (9), 2112-2115

  • Vinylogous Aldol Products from Chiral Crotylsilanes Obtained by Enantioselective Rh(II) and Cu(I) Carbenoid Si−H Insertion

    Jie Wu, Yu Chen and James S. Panek
    Organic Letters2010 12 (9), 2112-2115

    Enantioenriched homoallylic ethers containing a α,β-unsaturated ester (syn-vinylogous aldol products) were directly accessed by Lewis acid catalyzed crotylation utilizing chiral silane 2. The reagents were prepared by enantioselective Si−H insertion to ...

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

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