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Identification of diastereoisomers using VCD versus ECD and ORD: the stereochemistry of tadalafil

Author
Organization
Abstract
The absolute configuration of all 4 stereoisomers of Tadalafil is determined using vibrational circular dichroism (VCD), electric circular dichroism (ECD) and optical rotatory dispersion (ORD) spectroscopy. By comparing experimentally obtained VCD spectra to computationally simulated ones, the absolute configuration of the enantiomeric pair (6R, 12aR)/ (6S, 12aS) can be confidently assigned without a prior knowledge on their relative stereochemistry. For the other enantiomeric pair (6R, 12aS)/ (6S, 12aR), the absolute configuration is assigned after excluding the configuration already assigned to the enantiomeric pair (6R, 12aR)/(6S, 12aS). ECD and ORD spectra are also used to investigate the complementarity of the three chiroptical techniques. VCD spectroscopy is found to have advantages over ECD and ORD for identification of diastereoisomers.
Keywords
VCD chirality

Citation

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Chicago
Qiu, Shi, Wouter Herrebout, Ewoud De Gussem, Patrick Bultinck, and Sergey Sergeyev. 2012. “Identification of Diastereoisomers Using VCD Versus ECD and ORD: The Stereochemistry of Tadalafil.” In Vibrational Optical Activity : Interplay of Theory and Experiment, Abstracts.
APA
Qiu, S., Herrebout, W., De Gussem, E., Bultinck, P., & Sergeyev, S. (2012). Identification of diastereoisomers using VCD versus ECD and ORD: the stereochemistry of tadalafil. Vibrational Optical Activity : Interplay of Theory and Experiment, Abstracts. Presented at the Vibrational Optical Activity : Interplay of Theory and Experiment.
Vancouver
1.
Qiu S, Herrebout W, De Gussem E, Bultinck P, Sergeyev S. Identification of diastereoisomers using VCD versus ECD and ORD: the stereochemistry of tadalafil. Vibrational Optical Activity : Interplay of Theory and Experiment, Abstracts. 2012.
MLA
Qiu, Shi, Wouter Herrebout, Ewoud De Gussem, et al. “Identification of Diastereoisomers Using VCD Versus ECD and ORD: The Stereochemistry of Tadalafil.” Vibrational Optical Activity : Interplay of Theory and Experiment, Abstracts. 2012. Print.
@inproceedings{3002708,
  abstract     = {The absolute configuration of all 4 stereoisomers of Tadalafil is determined using vibrational circular dichroism (VCD), electric circular dichroism (ECD) and optical rotatory dispersion (ORD) spectroscopy. By comparing experimentally obtained VCD spectra to computationally simulated ones, the absolute configuration of the enantiomeric pair (6R, 12aR)/ (6S, 12aS) can be confidently assigned without a prior knowledge on their relative stereochemistry. For the other enantiomeric pair (6R, 12aS)/ (6S, 12aR), the absolute configuration is assigned after excluding the configuration already assigned to the enantiomeric pair (6R, 12aR)/(6S, 12aS). ECD and ORD spectra are also used to investigate the complementarity of the three chiroptical techniques. VCD spectroscopy is found to have advantages over ECD and ORD for identification of diastereoisomers.},
  author       = {Qiu, Shi and Herrebout, Wouter and De Gussem, Ewoud and Bultinck, Patrick and Sergeyev, Sergey},
  booktitle    = {Vibrational Optical Activity : Interplay of Theory and Experiment, Abstracts},
  keyword      = {VCD chirality},
  language     = {eng},
  location     = {Pisa, Italy},
  title        = {Identification of diastereoisomers using VCD versus ECD and ORD: the stereochemistry of tadalafil},
  year         = {2012},
}