86117-53-5Relevant articles and documents
Palladium-Catalyzed Modular Synthesis of Substituted Piperazines and Related Nitrogen Heterocycles
Montgomery, Thomas D.,Rawal, Viresh H.
supporting information, p. 740 - 743 (2016/03/01)
We report here a novel method for the modular synthesis of highly substituted piperazines and related bis-nitrogen heterocycles via a palladium-catalyzed cyclization reaction. The process couples two of the carbons of a propargyl unit with various diamine components to provide nitrogen heterocycles in generally good to excellent yields and high regio- and stereochemical control. (Chemical Equation Presented).
Oxazoline derivatives tagged with tosylated amino acids as recyclable organocatalysts for enantioselective allylation of aldehydes
Ghosh, Debashis,Sadhukhan, Arghya,Maity, Nabin Ch.,Abdi, Sayed H. R.,Khan, Noor-Ul H.,Kureshy, Rukhsana I.,Bajaj, Hari C.
, p. 12257 - 12265 (2014/03/21)
A series of amino acid-based oxazoline compounds have been prepared and successfully applied to the enantioselective allylation reaction of aldehydes. The fine-tuning of the structure of the oxazolines led to (S,S)-4 as an efficient organocatalyst which gave homoallyl alcohols in good yield (up to 90%) and excellent ee (up to 99%) for a wide range of substrates including aromatic, hetero-aromatic and α,β-unsaturated aldehydes. The chiral organocatalyst was synthesized in three easy steps with an overall 88% yield and successfully recycled for up to three cycles. On the basis of the experimental observations and NMR studies, a probable mechanism was proposed for this reaction.
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.
supporting information, p. 14224 - 14232 (2013/11/06)
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.