Practical Stereoselective Synthesis of β-Branched α-Amino Acids through Efficient Kinetic Resolution in the Phase-Transfer-Catalyzed Asymmetric Alkylations

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Abstract

Phase-transfer-catalyzed alkylation of glycinate Schiff base with racemic secondary alkyl halides proceeded with excellent levels of syn- and enantioselectivities under the influence of chiral quaternary ammonium bromide 1d and 18-crown-6. The alkylation product can be selectively converted to the corresponding anti isomer, allowing the preparation of all the stereoisomers of β-alkyl-α-amino acid derivatives, an extremely valuable chiral building block.

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This article has been cited by 3 ACS Journal articles (3 most recent appear below).

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  Novel Chiral Template for Preparation of α-Amino Acids: Practical Synthesis and Application

  Kazumi Okuro, Yasuhiro Saka, Ikuhiro Suzuki, and Masaru Mitsuda
  2009 1009 (), 89-100

  • Novel Chiral Template for Preparation of α-Amino Acids: Practical Synthesis and Application

    Kazumi Okuro, Yasuhiro Saka, Ikuhiro Suzuki, and Masaru Mitsuda
    2009 1009 (), 89-100

    A novel chiral imidazolidinone-type template for synthesizing optically active α-amino acids has been developed. The template was prepared from α-phenylethylamine as a chiral source, 2-chloroacetamide, and 2,6-dichlorobenzaldehyde in 4 steps. The process ...

    Abstract | Hi-Res PDF | PDF w/ Links
• 

  Highly Enantioselective Cu-Catalyzed Conjugate Addition−Elimination of Activated Allylic Acetates with Glycine Derivatives

  Chun-Gen Chen, Xue-Long Hou and Lin Pu
  Organic Letters2009 11 (10), 2073-2075

  • Highly Enantioselective Cu-Catalyzed Conjugate Addition−Elimination of Activated Allylic Acetates with Glycine Derivatives

    Chun-Gen Chen, Xue-Long Hou and Lin Pu
    Organic Letters2009 11 (10), 2073-2075

    The reaction of a glycinate Schiff base with the activated alkyl- and aryl-substituted allylic acetates afforded 4-alkylidenylglutamic acid derivatives in high yields and high enantioselectivities by using Cu/P,N-FcPhox as the catalyst.

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

  Second-Generation DBFOX Ligands for the Synthesis of β-Substituted α-Amino Acids via Enantioselective Radical Conjugate Additions

  Biplab Banerjee, Steven G. Capps, Junghoon Kang, Joshua W. Robinson and Steven L. Castle
  The Journal of Organic Chemistry2008 73 (22), 8973-8978

  • Second-Generation DBFOX Ligands for the Synthesis of β-Substituted α-Amino Acids via Enantioselective Radical Conjugate Additions

    Biplab Banerjee, Steven G. Capps, Junghoon Kang, Joshua W. Robinson and Steven L. Castle
    The Journal of Organic Chemistry2008 73 (22), 8973-8978

    A set of second-generation DBFOX ligands possessing extended aryl or benzyl-type groups was synthesized. The requisite amino alcohols were either commercially available (DBFOX/Bn) or constructed via Sharpless asymmetric aminohydroxylation (DBFOX/Nap, ...

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

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