Chemoenzymatic approach to optically active 4-hydroxy-5-alkylcyclopent-2-en-1-one derivatives: an application of a combined circular dichroism spectroscopy and DFT calculations to assignment of absolute configuration.
A series of representative optically active derivatives of 4-hydroxy-5-alkylcyclopent-2-en-1-one were prepared from the respective 2-furyl methyl carbinols via the Piancatelli rearrangement followed by the enzymatic kinetic resolution of racemates. Applicability of chiroptical methods (experimental and calculated electronic circular dichroism [ECD] and vibrational circular dichroism [VCD] spectra) to determine the absolute configuration of both stereogenic centers in 4-hydroxy-5-methylcyclopent-2-en-1-one was demonstrated. It was also demonstrated that the concurrent application of ECD and VCD spectroscopy can be used for the determination of the configuration of two stereogenic centers.
Institute of Organic Chemistry of the Polish Academy of Sciences, Warsaw, Poland.
Jadwiga
J
Frelek
Michał
M
Karchier
Daria
D
Madej
Karol
K
Michalak
Paweł
P
Różański
Jerzy
J
Wicha
D002175:Candida / Q000201:enzymology; D002942:Circular Dichroism; D003517:Cyclopentanes / Q000737:chemistry*; D006863:Hydrogen-Ion Concentration; D007700:Kinetics; D008049:Lipase / Q000737:chemistry; D009682:Magnetic Resonance Spectroscopy; D008958:Models, Molecular; D015233:Models, Statistical; D008968:Molecular Conformation; D013055:Spectrophotometry, Infrared; D013056:Spectrophotometry, Ultraviolet; D013237:Stereoisomerism
D003517:Cyclopentanes; D008049:Lipase
Candida antarctica lipase; Piancatelli rearrangement; chiral cyclopentenones; density functional theory; electronic circular dichroism; kinetic resolution; vibrational circular dichroism