Publication
Title
Synthesis of the natural product building block 5-(3-bromophenyl)-4-hydroxy-5-methylhexan-2-one and its chiral characterization by using chiroptical spectroscopy
Author
Abstract
The absolute configuration of 5-(3-bromophenyl)-4-hydroxy-5-methylhexan-2-one, an intermediate in the synthesis of various natural products, is assigned by using vibrational circular dichroism (VCD), electronic circular dichroism (ECD), and optical rotatory dispersion (ORD). Experimental spectra were compared to density functional theory (DFT) calculations of the molecule with known configuration. These three techniques independently confirm that the absolute configuration is (S)-5-(3-bromophenyl)-4-hydroxy-5-methylhexan-2-one, thus enabling us to assign the absolute configuration with high reliability. The reliability of the VCD analysis was assessed quantitatively by using the CompareVOA program. We found that, in cases in which the agreement between theory and experiment was very good, a value of 10 cm(-1) for the triangular weighting function gave a more-realistic discriminative power between enantiomers than the default value of 20 cm(-1).
Language
English
Source (journal)
ChemPhysChem: a European journal of chemical physics and physical chemistry. - Weinheim
Publication
Weinheim : 2013
ISSN
1439-4235
Volume/pages
14:14(2013), p. 3255-3262
ISI
000325157100019
Full text (Publishers DOI)
UAntwerpen
Faculty/Department
Research group
Publication type
Subject
Affiliation
Publications with a UAntwerp address
External links
Web of Science
Record
Identification
Creation 08.11.2013
Last edited 01.04.2017
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