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Enantiopure 2,9-Dideuterodecane – Preparation and Proof of Enantiopurity

Lookup NU author(s): Dr Miriam Fsadni, Amy Roberts, Professor Majid Sadeghi, Emeritus Professor Bernard Golding

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Abstract

© 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.

Publication metadata

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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