226699-01-0Relevant articles and documents
Synthesis of enantiomerically pure α-[4-(1-substituted)-1,2,3-triazol-4-yl]-benzylacetamides via microwave-assisted click chemistry: towards new potential antimicrobial agents
Castagnolo, Daniele,Dessi, Filippo,Radi, Marco,Botta, Maurizio
, p. 1345 - 1350 (2008/02/10)
Chiral 1-phenyl-2-propynylamines are important building blocks for the synthesis of antifungal and antiaromatase agents related to bifonazole. In this report, a microwave-assisted Cu(I)-catalyzed 'click chemistry' approach has been employed to easily generate a small library of enantiomerically pure α-[4-(1-substituted)-1,2,3-triazol-4-yl]benzylacetamides starting from racemic propargylamines. These compounds could represent easily accessible intermediates for the synthesis of new antimicrobial agents.
Microwave-assisted ethylene-alkyne cross-metathesis: Synthesis of chiral 2-(N-1-acetyl-1-arylmethyl)-1,3-butadienes
Castagnolo, Daniele,Renzulli, Michela L.,Galletti, Elena,Corelli, Federico,Botta, Maurizio
, p. 2893 - 2896 (2007/10/03)
Chiral 1-arylpropargyl amides, which are resistant to undergoing ethylene-alkyne cross-metathesis at atmospheric pressure, were reacted under microwave irradiation to afford enantiomerically enriched 2-(N-1-acetyl-1- arylmethyl)-1,3-butadienes within a fe
Resolution of β-unsaturated amines with isopropylidene glycerol hydrogen phthalate
Pallavicini, Marco,Valoti, Ermanno,Villa, Luigi,Piccolo, Oreste
, p. 4017 - 4025 (2007/10/03)
1-Phenyl-2-propenylamine 2, 1-phenyl-2-propinylamine 3, 1-(1-cyclohexenyl)ethylamine 4, (E)-2-ethylidenecyclohexylamine 5 and α-methylallylamine hydrochloride 6 were selected as candidates for resolution with isopropylidene glycerol hydrogen phthalate 1, previously described as an efficient resolving agent of 1-arylalkylamines. With only the exception of 5, all these substrates were resolved by (S)-1. In particular both the enantiomers of 2 and 3 were obtained in excellent yields and with very high enantiomeric excesses. The absolute configurations of non-racemic forms of 2, 3 and 4, not prepared before except those of 3, were established by correlation with the respective hydrogenation products. The enantiomeric excesses of all the resolved substrates were accurately determined by chiral HPLC analysis. The fact that 1 resolves 4 and 6 but not their saturated analogues and shows higher efficiency in resolving 2 and 3 than 1-phenylpropylamine indicates the positive influence of the presence of β-unsaturation on the resolvability of aminic substrates with such an acid. Copyright (C) 2000 Elsevier Science Ltd.