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Application of deuterated THENA for assigning the absolute configuration of chiral secondary alcohols


Soponpong, Jakapun; Dolsophon, Kulvadee; Thongpanchang, Chawanee; Linden, Anthony; Thongpanchang, Tienthong (2019). Application of deuterated THENA for assigning the absolute configuration of chiral secondary alcohols. Tetrahedron Letters, 60(6):497-500.

Abstract

The structure of a constrained bicyclic CDA, 1,2,3,4-tetrahydro-1,4-epoxynaphthalene-1-carboxylic acid, THENA 1, was modified by replacing both exo-methylene protons with deuterium atoms. The modified CDA, THENA-d2 2, was successfully prepared and could be used to assign the absolute configuration of chiral secondary alcohols with good reliability. Compared with THENA, the multiplicity of the methylene proton signals in the 1H NMR spectra of THENA-d2 derivatives is less complicated and the new CDA thus offers simpler NMR spectra for data interpretation.

Abstract

The structure of a constrained bicyclic CDA, 1,2,3,4-tetrahydro-1,4-epoxynaphthalene-1-carboxylic acid, THENA 1, was modified by replacing both exo-methylene protons with deuterium atoms. The modified CDA, THENA-d2 2, was successfully prepared and could be used to assign the absolute configuration of chiral secondary alcohols with good reliability. Compared with THENA, the multiplicity of the methylene proton signals in the 1H NMR spectra of THENA-d2 derivatives is less complicated and the new CDA thus offers simpler NMR spectra for data interpretation.

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Additional indexing

Item Type:Journal Article, refereed, original work
Communities & Collections:07 Faculty of Science > Department of Chemistry
Dewey Decimal Classification:540 Chemistry
Uncontrolled Keywords:Organic Chemistry, Biochemistry, Drug Discovery, Constrained bicycle, Chiral derivatizing agent, Diels Alder reaction, Deuterated molecule
Language:English
Date:1 February 2019
Deposited On:13 Feb 2019 15:38
Last Modified:13 Feb 2019 16:02
Publisher:Elsevier
ISSN:0040-4039
OA Status:Closed
Publisher DOI:https://doi.org/10.1016/j.tetlet.2019.01.013
Project Information:
  • : FunderFaculty of Science, Mahidol University, Thailand
  • : Grant IDBRG5480020
  • : Project Title
  • : FunderThailand Research Fund
  • : Grant ID
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  • : FunderDevelopment of Pharmaceuticals from Bioresources and Its Management (NRU)
  • : Grant ID
  • : Project Title
  • : FunderCenter of Excellence for Innovation in Chemistry (PERCH-CIC)
  • : Grant ID
  • : Project Title

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