1374035-93-4Relevant academic research and scientific papers
Oxazoline-based organocatalyst for enantioselective strecker reactions: A protocol for the synthesis of levamisole
Sadhukhan, Arghya,Sahu, Debashis,Ganguly, Bishwajit,Khan, Noor-Ul H.,Kureshy, Rukhsana I.,Abdi, Sayed H.R.,Suresh,Bajaj, Hari C.
, p. 14224 - 14232 (2013)
A chiral oxazoline-based or-ganocatalyst has been found to efficiently catalyze asymmetric Strecker reactions of various aromatic and aliphatic N-benzhydrylimines with trime-thylsilyl cyanide (TMSCN) as a cyanide source at -20°C to give α-aminoni-triles in high yield (96%) with excellent chiral induction (up to 98% ee). DFT calculations have been performed to rationalize the enantioselective formation of the product with the organo-catalyst in these reactions. The organo-catalyst has been characterized by single-crystal X-ray diffraction analysis, as well as by other analytical methods. This protocol has been extended to the synthesis of the pharmaceutically important drug molecule levamisole in high yield and with high enantioselectivity.
C2-symmetric recyclable organocatalyst for enantioselective Strecker reaction for the synthesis of α-amino acid and chiral diamine-an intermediate for APN inhibitor
Saravanan,Sadhukhan, Arghya,Khan, Noor-Ul H.,Kureshy, Rukhsana I.,Abdi, Sayed H. R.,Bajaj, Hari C.
experimental part, p. 4375 - 4384 (2012/06/30)
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.
