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Determination of the Absolute Configuration of (S )-N -(1-Aryl-allyl)-3, 5-dinitrobenzamides and Their Elution Order on Brush-Type Chiral Stationary Phases (CROSBI ID 253587)

Prilog u časopisu | izvorni znanstveni rad | međunarodna recenzija

Knežević, Anamarija ; Novak, Jurica ; Pescitelli, Gennaro ; Vinković, Vladimir Determination of the Absolute Configuration of (S )-N -(1-Aryl-allyl)-3, 5-dinitrobenzamides and Their Elution Order on Brush-Type Chiral Stationary Phases // European journal of organic chemistry, 2018 (2018), 19; 3982-3991. doi: 10.1002/ejoc.201800346

Podaci o odgovornosti

Knežević, Anamarija ; Novak, Jurica ; Pescitelli, Gennaro ; Vinković, Vladimir

engleski

Determination of the Absolute Configuration of (S )-N -(1-Aryl-allyl)-3, 5-dinitrobenzamides and Their Elution Order on Brush-Type Chiral Stationary Phases

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.

Ab initio calculations ; Chiral resolution ; Circular dichroism ; Configuration determination ; Liquid chromatography

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Podaci o izdanju

2018 (19)

2018.

3982-3991

objavljeno

1434-193X

1099-0690

10.1002/ejoc.201800346

Povezanost rada

Kemija

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