Chirality sensing of bioactive compounds with amino alcohol unit via circular dichroism

• Published in: Chirality (New York, N.Y.) Vol. 29; no. 10; pp. 589 - 598
• Main Authors: Górecki, Marcin, Groszek, Grażyna, Frelek, Jadwiga
• Format: Journal Article
• Language: English
• Published: United States Wiley Subscription Services, Inc 01.10.2017
• Subjects: 1,2‐amino alcohols; 1,3‐amino alcohols; Absolute configuration; Alcohols; Alkaloids; auxiliary chromophore; Bioactive compounds; Chirality; Circular dichroism; Configurations; Dichroism; dirhodium tetraacetate; Organic chemistry; Rhodium compounds; Spectroscopy; dirhodium tetraacetate; auxiliary chromophore; circular dichroism; absolute configuration; 1,2-amino alcohols; 1,3-amino alcohols
• ISSN: 0899-0042; 1520-636X; 1520-636X
• DOI: 10.1002/chir.22736

The aim of the present work was to test various chiroptical techniques, including in particular the in situ dirhodium methodology, to assign the absolute configuration of 1,2‐ and 1,3‐amino alcohols. As models, we selected mainly compounds that have both an additional strongly absorbing and interfering chromophoric system and application in medicinal chemistry. Determination of the absolute configuration (AC) of the tested molecules such as cinchona alkaloids, Tamiflu, and others was carried out using a combination of electronic and vibrational circular dichroism (ECD, VCD) spectroscopy. It has been demonstrated that both 1,2‐ and 1,3‐aminol moieties are subject to the same sector rule correlating stereostructure of formed Rh2‐complex with chiroptical properties, and that the changes in the position of the stereogenic center do not affect its proper use.