1266583-84-9Relevant academic research and scientific papers
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)
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.
Modular amino acids and β-amino alcohol-based chiral ligands for enantioselective addition of diethylzinc to aromatic aldehydes
Gou, Shaohua,Ye, Zhongbin,Gou, Guangjun,Feng, Mingming,Chang, Jing
experimental part, p. 110 - 116 (2012/06/18)
Enantioselective addition of diethylzinc to a series of aromatic aldehydes was developed using a modular amino acids and ${bf beta}$-amino alcohol-based chiral ligand (2R)-N-[(1R,2S)-1-hydroxy-1-phenylpropan-2-yl]-3- phenyl-2-(tosylamino) propanamide (1f) without using titanium complex. The catalytic system employing 15 mol% of 1f was found to promote the addition of diethylzinc (ZnEt2) to a wide range of aromatic aldehydes with electron-donating and electron-withdrawing substituents, giving up to 97% ee of the corresponding secondary alcohol under mild conditions.
