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Lookup NU author(s): Miriam Fsadni, Amy Roberts, Professor Majid Sadeghi, Emeritus Professor Bernard Golding
This work is licensed under a Creative Commons Attribution-NonCommercial-NoDerivatives 4.0 International License (CC BY-NC-ND).
© 2021 The Authors. European Journal of Organic Chemistry published by Wiley-VCH GmbH(R,R)- and (S,S)-(2,9-2H2)-n-Decane were prepared regio- and stereospecifically in 25–26 % yield over five steps from commercially available enantiopure (R)- and (S)-propylene oxide, respectively. The synthetic procedure involved nucleophilic displacement of (R)- and (S)-4-toluenesulfonic acid 1-methyl-4-pentenyl ester with LiAlD4 to furnish the respective (5-2H)-1-hexenes. Subsequent olefin metathesis and reduction of the double bond furnished the title compounds. The optical purity of (R,R)- and (S,S)-(2,9-2H2)-n-decane could not be determined by chromatography or polarimetry. Therefore, (R,R)- and (R,S)-(5-2H)-3-hydroxy-2-hexanone were prepared from their respective hexenes by Wacker oxidation, followed by enantioselective α-hydroxylation. The enantiopurity could then be determined by NMR spectroscopy because the stereospecifically deuterated hydroxyketones showed separated signals for the subterminal carbon atom (C-5) in the 13C NMR spectrum.
Author(s): Mitschke N, Erucar G, Fsadni MH, Roberts AR, Sadeghi MM, Golding BT, Christoffers J, Wilkes H
Publication type: Article
Publication status: Published
Journal: European Journal of Organic Chemistry
Year: 2021
Volume: 2021
Issue: 27
Pages: 3854-3863
Print publication date: 22/07/2021
Online publication date: 10/06/2021
Acceptance date: 09/06/2021
Date deposited: 08/09/2021
ISSN (print): 1434-193X
ISSN (electronic): 1099-0690
Publisher: John Wiley and Sons Inc
URL: https://doi.org/10.1002/ejoc.202100360
DOI: 10.1002/ejoc.202100360
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