TY - JOUR T1 - Oxazoline-based organocatalyst for enantioselective strecker reactions: a protocol for the synthesis of levamisole. AU - Sadhukhan,Arghya, AU - Sahu,Debashis, AU - Ganguly,Bishwajit, AU - Khan,Noor-ul H, AU - Kureshy,Rukhsana I, AU - Abdi,Sayed H R, AU - Suresh,E, AU - Bajaj,Hari C, Y1 - 2013/09/05/ PY - 2013/05/24/received PY - 2013/06/27/revised PY - 2013/9/7/entrez PY - 2013/9/7/pubmed PY - 2015/3/31/medline KW - Strecker reaction KW - aminonitriles KW - enantioselectivity KW - organocatalysis KW - oxazoline SP - 14224 EP - 32 JF - Chemistry (Weinheim an der Bergstrasse, Germany) JO - Chemistry VL - 19 IS - 42 N2 - A chiral oxazoline-based organocatalyst has been found to efficiently catalyze asymmetric Strecker reactions of various aromatic and aliphatic N-benzhydrylimines with trimethylsilyl cyanide (TMSCN) as a cyanide source at -20 °C to give α-aminonitriles 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 organocatalyst in these reactions. The organocatalyst 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. SN - 1521-3765 UR - https://www.unboundmedicine.com/medline/citation/24009109/Oxazoline_based_organocatalyst_for_enantioselective_strecker_reactions:_a_protocol_for_the_synthesis_of_levamisole_ DB - PRIME DP - Unbound Medicine ER -