Determination of absolute configuration of conformationally flexible cis-dihydrodiol metabolites: Effect of diene substitution pattern on the circular dichroism spectra and optical rotations

M. Kwit, Narain Sharma, Derek Boyd, J. Gawronski

Research output: Contribution to journalArticle

18 Citations (Scopus)

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 languageEnglish
Pages (from-to)609-620
Number of pages12
JournalChirality
Volume20 (5)
Issue number5
DOIs
Publication statusPublished - 15 Oct 2008

ASJC Scopus subject areas

  • Analytical Chemistry
  • Organic Chemistry
  • Drug Discovery
  • Pharmacology

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