Premium
Chirality sensing of bioactive compounds with amino alcohol unit via circular dichroism
Author(s) -
Górecki Marcin,
Groszek Grażyna,
Frelek Jadwiga
Publication year - 2017
Publication title -
chirality
Language(s) - English
Resource type - Journals
SCImago Journal Rank - 0.43
H-Index - 77
eISSN - 1520-636X
pISSN - 0899-0042
DOI - 10.1002/chir.22736
Subject(s) - stereocenter , chemistry , absolute configuration , circular dichroism , chirality (physics) , vibrational circular dichroism , optical rotation , stereochemistry , molecule , spectroscopy , alcohol , organic chemistry , enantioselective synthesis , chiral symmetry , catalysis , nambu–jona lasinio model , physics , quantum mechanics , quark
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 Rh 2 ‐complex with chiroptical properties, and that the changes in the position of the stereogenic center do not affect its proper use.