Practical Asymmetric Henry Reaction Catalyzed by a Chiral Diamine-Cu(OAc)₂ Complex

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Abstract

The chiral diamine ligand 3 was designed and synthesized from (R,R)-1,2-diphenylethylenediamine, (S)-2,2‘-dibromomethyl-1,1‘-binaphthalene, and o-xylylene dibromide. The resulting 3-Cu(OAc)₂ complex was a highly efficient catalyst for the Henry reaction, giving the various nitroaldols with over 90% ee (up to >99%). The reaction was performed in n-propyl alcohol at room temperature, and the Henry adducts were produced in high yield with excellent enantiomeric excess; these attributes are desirable in a catalyst for practical use.

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This article has been cited by 19 ACS Journal articles (5 most recent appear below).

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  Cu(II)-Macrocylic [H₄]Salen Catalyzed Asymmetric Nitroaldol Reaction and Its Application in the Synthesis of α1-Adrenergic Receptor Agonist (R)-Phenylephrine

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  ACS Catalysis2011 1 (11), 1529-1535

  • Cu(II)-Macrocylic [H₄]Salen Catalyzed Asymmetric Nitroaldol Reaction and Its Application in the Synthesis of α1-Adrenergic Receptor Agonist (R)-Phenylephrine

    Rukhsana I. Kureshy, Anjan Das, Noor-ul H. Khan, Sayed H. R. Abdi, and Hari C. Bajaj
    ACS Catalysis2011 1 (11), 1529-1535

    New chiral Cu (II) complexes 1–6 were generated in situ by the interaction of different sources of copper(II) salts with chiral monomeric and dimeric macrocyclic [H4]salen ligands derived from (1R,2R)-(−)-1,2-diaminocyclohexane and (1R,2R)-(−)-1,2-...

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

  Asymmetric Synthesis of an Antagonist of Neurokinin Receptors: SSR 241586

  Thomas-Xavier Métro, Anne Cochi, Domingo Gomez Pardo, and Janine Cossy
  The Journal of Organic Chemistry2011 76 (8), 2594-2602

  • Asymmetric Synthesis of an Antagonist of Neurokinin Receptors: SSR 241586

    Thomas-Xavier Métro, Anne Cochi, Domingo Gomez Pardo, and Janine Cossy
    The Journal of Organic Chemistry2011 76 (8), 2594-2602

    SSR 241586 is a 2,2-disubstituted morpholine, developed by Sanofi-Aventis, which is active in the treatment of schizophrenia and irritable bowel syndrome (IBS). Different strategies have been studied to synthesize this molecule and among the strategies an ...

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

  Pyrrole Macrocyclic Ligands for Cu-Catalyzed Asymmetric Henry Reactions

  Andrea Gualandi, Lucia Cerisoli, Helen Stoeckli-Evans, and Diego Savoia
  The Journal of Organic Chemistry2011 Article ASAP

  • Pyrrole Macrocyclic Ligands for Cu-Catalyzed Asymmetric Henry Reactions

    Andrea Gualandi, Lucia Cerisoli, Helen Stoeckli-Evans, and Diego Savoia
    The Journal of Organic Chemistry2011 Article ASAP

    New chiral perazamacrocycles containing four pyrrole rings have been synthesized by the [2 + 2] condensation of (R,R)-diaminocyclohexane and 5,5′-(alkane-2,2-diyl)bis(1H-pyrrole-2-carbaldehydes). These macrocycles, differing for the alkyl/aryl meso-...

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

  Synthesis of C₁-Symmetric Chiral Secondary Diamines and Their Applications in the Asymmetric Copper(II)-Catalyzed Henry (Nitroaldol) Reactions

  Yirong Zhou, Junfang Dong, Fanglin Zhang, and Yuefa Gong
  The Journal of Organic Chemistry2011 76 (2), 588-600

  • Synthesis of C₁-Symmetric Chiral Secondary Diamines and Their Applications in the Asymmetric Copper(II)-Catalyzed Henry (Nitroaldol) Reactions

    Yirong Zhou, Junfang Dong, Fanglin Zhang, and Yuefa Gong
    The Journal of Organic Chemistry2011 76 (2), 588-600

    A small library of C1-symmetric chiral diamines (L1−L9) was constructed via condensing exo-(−)-bornylamine or (+)-(1S,2S,5R)-menthylamine with various Cbz-protected amino acids. Among them, ligand L1/CuCl2·2H2O complex (2.5 mol %) shows outstanding ...

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

  A Highly Diastereo- and Enantioselective Copper(I)-Catalyzed Henry Reaction Using a Bis(sulfonamide)−Diamine Ligand

  Wei Jin, Xincheng Li, and Boshun Wan
  The Journal of Organic Chemistry2011 76 (2), 484-491

  • A Highly Diastereo- and Enantioselective Copper(I)-Catalyzed Henry Reaction Using a Bis(sulfonamide)−Diamine Ligand

    Wei Jin, Xincheng Li, and Boshun Wan
    The Journal of Organic Chemistry2011 76 (2), 484-491

    A series of bis(sulfonamide)−diamine (BSDA) ligands were synthesized from commercially available chiral α-amino alcohols and diamines. The chiral BSDA ligand 3a, coordinated with Cu(I), catalyzes the enantioselective Henry reaction with excellent ...

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

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