title: C2-symmetric recyclable organocatalyst for enantioselective Strecker reaction for the synthesis of α-amino acid and chiral diamine--an intermediate for APN inhibitor.
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.
authors.affiliation: 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.
authors.forename: S
authors.initials: S
authors.lastname: Saravanan
authors.forename: Arghya
authors.initials: A
authors.lastname: Sadhukhan
authors.forename: Noor-ul H
authors.initials: NU
authors.lastname: Khan
authors.forename: Rukhsana I
authors.initials: RI
authors.lastname: Kureshy
authors.forename: Sayed H R
authors.initials: SH
authors.lastname: Abdi
authors.forename: Hari C
authors.initials: HC
authors.lastname: Bajaj
mesh_terms: D000596:Amino Acids / Q000138:chemical synthesis* / Q000737:chemistry*; D018826:CD13 Antigens / Q000037:antagonists & inhibitors* / Q000737:chemistry*; D002384:Catalysis; D003959:Diamines / Q000138:chemical synthesis / Q000737:chemistry* / Q000494:pharmacology; D015394:Molecular Structure; D009570:Nitriles / Q000737:chemistry*; D013237:Stereoisomerism
chemical_list: C575058:(R)-3-phenylpropane-1,2-diame; D000596:Amino Acids; D003959:Diamines; D009570:Nitriles; D018826:CD13 Antigens