Determination of absolute configuration using vibrational circular dichroism spectroscopy: The chiral sulfoxide 1‐thiochromanone S‐oxide
2002; Wiley; Volume: 14; Issue: 5 Linguagem: Inglês
10.1002/chir.10103
ISSN1520-636X
AutoresF. J. Devlin, Philip J. Stephens, Patrizia Scafato, Stefano Superchi, Carlo Rosini,
Tópico(s)Axial and Atropisomeric Chirality Synthesis
ResumoWe reexamined the absolute configuration (AC) of the chiral sulfoxide 1-thiochromanone S-oxide (1) using vibrational circular dichroism (VCD) spectroscopy. The VCD spectrum of 1 was analyzed using density functional theory (DFT). DFT predicts two stable conformations of 1, separated by <1 kcal/mole. Their VCD spectra were calculated using the DFT/GIAO methodology. The VCD spectrum predicted for the equilibrium mixture of the two conformations of (S)-1 is in excellent agreement with the experimental spectrum of (+)-1. The AC of 1 is therefore definitively R(-)/S(+).
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