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 |
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Authors: | Jadwiga Frelek Micha? Karchier Daria Madej Karol Michalak Pawe? Ró?ański Jerzy Wicha |
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Institution: | Institute of Organic Chemistry of the Polish Academy of Sciences, Warsaw, Poland |
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Abstract: | 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. Chirality 26:300–306, 2014. © 2014 Wiley Periodicals, Inc. |
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Keywords: | chiral cyclopentenones Piancatelli rearrangement kinetic resolution Candida antarctica lipase density functional theory electronic circular dichroism vibrational circular dichroism |
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