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 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
Faculty/Department
Faculty of Sciences. Chemistry
Publication type
article
Publication
Weinheim ,
Subject
Physics
Chemistry
Source (journal)
ChemPhysChem: a European journal of chemical physics and physical chemistry. - Weinheim
Volume/pages
14(2013) :14 , p. 3255-3262
ISSN
1439-4235
1439-4235
ISI
000325157100019
Carrier
E
Target language
English (eng)
Full text (Publishers DOI)
Affiliation
University of Antwerp
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).
E-info
http://gateway.webofknowledge.com/gateway/Gateway.cgi?GWVersion=2&SrcApp=PARTNER_APP&SrcAuth=LinksAMR&KeyUT=WOS:000325157100019&DestLinkType=RelatedRecords&DestApp=ALL_WOS&UsrCustomerID=ef845e08c439e550330acc77c7d2d848
http://gateway.webofknowledge.com/gateway/Gateway.cgi?GWVersion=2&SrcApp=PARTNER_APP&SrcAuth=LinksAMR&KeyUT=WOS:000325157100019&DestLinkType=FullRecord&DestApp=ALL_WOS&UsrCustomerID=ef845e08c439e550330acc77c7d2d848
http://gateway.webofknowledge.com/gateway/Gateway.cgi?GWVersion=2&SrcApp=PARTNER_APP&SrcAuth=LinksAMR&KeyUT=WOS:000325157100019&DestLinkType=CitingArticles&DestApp=ALL_WOS&UsrCustomerID=ef845e08c439e550330acc77c7d2d848
Handle