Oxazoline‐Based Organocatalyst for Enantioselective Strecker Reactions: A Protocol for the Synthesis of Levamisole. Issue 42 (5th September 2013)

• Record Type: Journal Article
• Authors: Sadhukhan, Arghya; Sahu, Debashis; Ganguly, Bishwajit; Khan, Noor‐ul H.; Kureshy, Rukhsana I.; Abdi, Sayed H. R.; Suresh, E.; Bajaj, Hari C.
• Is Part Of: Chemistry. Volume 19:Issue 42(2013)
• Page Start: 14224
• Page End: 14232
• Publication Date: 2013-09-05
• Subjects: Chemistry -- Periodicals; 540
• DOI: 10.1002/chem.201302007
• Languages: English
• ISSNs: 0947-6539

Abstract

<abstract abstract-type="main" xml:lang="en"> <title>Abstract</title> <p>A chiral oxazoline‐based organocatalyst has been found to efficiently catalyze asymmetric Strecker reactions of various aromatic and aliphatic <italic>N</italic>‐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 % <italic>ee</italic>). 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.</p> </abstract>