688362-52-9Relevant academic research and scientific papers
Determination of the Absolute Configuration of (S)-N-(1-Aryl-allyl)-3,5-dinitrobenzamides and Their Elution Order on Brush-Type Chiral Stationary Phases
Kne?evi?, Anamarija,Novak, Jurica,Pescitelli, Gennaro,Vinkovi?, Vladimir
, p. 3982 - 3991 (2018/08/07)
A series of ten enantiomerically pure (S)-N-(1-aryl-allyl)-3,5-dinitrobenzamides (S-DNBs) was prepared using enzymatic resolution and chiral chromatography. Enzymatic resolution of corresponding 1-aryl-allylamines using Candida antarctica lipase B (CaLB) was efficient for amines with no steric hindrance near the stereogenic center and S-DNB amides were prepared by acylation of the obtained S-amine. When steric effects interrupted enzymatic resolution, racemic DNB amides were resolved using a brush-type chiral column (CSP-A) developed in our laboratory. Previously reported behavior of CaLB in kinetic resolution of amines was considered a starting point for the determination of absolute configuration (AC). The AC of prepared S-DNB amides was anticipated using the elution order of prepared DNB amides on CSP-A and commercial Whelk-O1 columns and comparison with DNB amides obtained after acylation of (S)-amines. The comparison between experimental electronic circular dichroism (ECD) spectra with those obtained by conformational analysis and ECD calculations of representative compounds allowed us to verify the AC of prepared DNB amides.
Enantioselective synthesis of 1-aryl-2-propenylamines: A new approach to a stereoselective synthesis of the Taxol side chain
Castagnolo, Daniele,Armaroli, Silvia,Corelli, Federico,Botta, Maurizio
, p. 941 - 949 (2007/10/03)
A variety of substituted 1-aryl-2-propenylamines of high enantiomeric purity were prepared via lipase-catalysed resolution of the corresponding racemates. (R)-1-Phenyl-2-propenylamine was further synthesised into (2R,3S)-3-benzoylamino-2-hydroxy-3-phenylpropanoic acid methyl ester, the side chain of Taxol.
