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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
- Source :
- The Journal of organic chemistry. 77(9)
- Publication Year :
- 2012
-
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.
- Subjects :
- chemistry.chemical_classification
Molecular Structure
Chemistry
Cyanide
Organic Chemistry
Strecker amino acid synthesis
Enantioselective synthesis
Stereoisomerism
CD13 Antigens
Diamines
Catalysis
Amino acid
chemistry.chemical_compound
Yield (chemistry)
Amide
Nitriles
Organic chemistry
Amino Acids
Subjects
Details
- ISSN :
- 15206904
- Volume :
- 77
- Issue :
- 9
- Database :
- OpenAIRE
- Journal :
- The Journal of organic chemistry
- Accession number :
- edsair.doi.dedup.....d1ba50f2f68a823428c7c0053e4d7d60