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C2-symmetric recyclable organocatalyst for enantioselective Strecker reaction for the synthesis of α-amino acid and chiral diamine--an intermediate for APN inhibitor.
J Org Chem. 2012 May 04; 77(9):4375-84.JO

Abstract

Recyclable chiral amide-based organocatalyst 5 efficiently catalyzed asymmetric Strecker reaction of various aromatic and aliphatic N-benzhydrylimines with ethyl cyanoformate as cyanide source at -10 °C to give a high yield (95%) of α-aminonitriles with excellent chiral induction (ee, up to 99%) with the added advantage of recyclability. Based on experimental observations a probable mechanism was proposed for this reaction. This protocol with catalyst 5 was extended for the synthesis of (R)-phenylalanine and pharmaceutically important drug intermediate (R)-3-phenylpropane-1,2-diamine in high yield with high enantioselectivity.

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Publisher Full Text (DOI)

Authors+Show Affiliations

Saravanan S
Discipline of Inorganic Materials and Catalysis, Central Salt and Marine Chemicals Research Institute, Council of Scientific & Industrial Research, G. B. Marg, Bhavnagar 364 021, Gujarat, India.
Sadhukhan A
No affiliation info available
Khan NU
No affiliation info available
Kureshy RI
No affiliation info available
Abdi SH
No affiliation info available
Bajaj HC
No affiliation info available

MeSH

Amino AcidsCD13 AntigensCatalysisDiaminesMolecular StructureNitrilesStereoisomerism

Pub Type(s)

Journal Article
Research Support, Non-U.S. Gov't

Language

eng

PubMed ID

22497557

Citation

Saravanan, S, et al. "C2-symmetric Recyclable Organocatalyst for Enantioselective Strecker Reaction for the Synthesis of Α-amino Acid and Chiral Diamine--an Intermediate for APN Inhibitor." The Journal of Organic Chemistry, vol. 77, no. 9, 2012, pp. 4375-84.
Saravanan S, Sadhukhan A, Khan NU, et al. C2-symmetric recyclable organocatalyst for enantioselective Strecker reaction for the synthesis of α-amino acid and chiral diamine--an intermediate for APN inhibitor. J Org Chem. 2012;77(9):4375-84.
Saravanan, S., Sadhukhan, A., Khan, N. U., Kureshy, R. I., Abdi, S. H., & Bajaj, H. C. (2012). C2-symmetric recyclable organocatalyst for enantioselective Strecker reaction for the synthesis of α-amino acid and chiral diamine--an intermediate for APN inhibitor. The Journal of Organic Chemistry, 77(9), 4375-84. https://doi.org/10.1021/jo300349f
Saravanan S, et al. C2-symmetric Recyclable Organocatalyst for Enantioselective Strecker Reaction for the Synthesis of Α-amino Acid and Chiral Diamine--an Intermediate for APN Inhibitor. J Org Chem. 2012 May 4;77(9):4375-84. PubMed PMID: 22497557.
* Article titles in AMA citation format should be in sentence-case
TY - JOUR T1 - C2-symmetric recyclable organocatalyst for enantioselective Strecker reaction for the synthesis of α-amino acid and chiral diamine--an intermediate for APN inhibitor. AU - Saravanan,S, AU - Sadhukhan,Arghya, AU - Khan,Noor-ul H, AU - Kureshy,Rukhsana I, AU - Abdi,Sayed H R, AU - Bajaj,Hari C, Y1 - 2012/04/22/ PY - 2012/4/14/entrez PY - 2012/4/14/pubmed PY - 2012/9/29/medline SP - 4375 EP - 84 JF - The Journal of organic chemistry JO - J Org Chem VL - 77 IS - 9 N2 - Recyclable chiral amide-based organocatalyst 5 efficiently catalyzed asymmetric Strecker reaction of various aromatic and aliphatic N-benzhydrylimines with ethyl cyanoformate as cyanide source at -10 °C to give a high yield (95%) of α-aminonitriles with excellent chiral induction (ee, up to 99%) with the added advantage of recyclability. Based on experimental observations a probable mechanism was proposed for this reaction. This protocol with catalyst 5 was extended for the synthesis of (R)-phenylalanine and pharmaceutically important drug intermediate (R)-3-phenylpropane-1,2-diamine in high yield with high enantioselectivity. SN - 1520-6904 UR - https://www.unboundmedicine.com/medline/citation/22497557/C2_symmetric_recyclable_organocatalyst_for_enantioselective_Strecker_reaction_for_the_synthesis_of_α_amino_acid_and_chiral_diamine__an_intermediate_for_APN_inhibitor_ L2 - https://doi.org/10.1021/jo300349f DB - PRIME DP - Unbound Medicine ER -