Abstract
Absolute configurations of a number of cis-dihydrodiols (cis-1,2-dihydroxy-3,5-cyclohexadienes), synthetically useful products of TDO-catalyzed dihydroxylations of 1,2- and 1,3-disubstituted benzene derivatives, have been determined by a comparison of calculated and experimental CD spectra and optical rotations and by methods involving X-ray crystallography, H-1 NMR spectra of diastereoisomeric derivatives, and by stereochemical correlations. The computations disclosed a significant effect of the substituents on conformational equilibria of cis-dihydrodiols and chiroptical properties of individual conformers. The assigned absolute configurations of cis-dihydrodiols have allowed the validity of a simple predictive model for TDO-catalyzed arene dihydroxylations to be extended.
Original language | English |
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Pages (from-to) | 609-620 |
Number of pages | 12 |
Journal | Chirality |
Volume | 20 (5) |
Issue number | 5 |
DOIs | |
Publication status | Published - 15 Oct 2008 |
ASJC Scopus subject areas
- Analytical Chemistry
- Organic Chemistry
- Drug Discovery
- Pharmacology