Application of deuterated THENA for assigning the absolute configuration of chiral secondary alcohols |
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| Authors: | Jakapun Soponpong Kulvadee Dolsophon Chawanee Thongpanchang Anthony Linden Tienthong Thongpanchang |
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| Institution: | 1. Department of Chemistry and Center of Excellence for Innovation in Chemistry (PERCH-CIC), Faculty of Science, Mahidol University, Rama 6 Road, Bangkok 10400, Thailand;2. Department of Chemistry, Faculty of Science, Srinakharinwirot University, 114 Sukhumvit 23, Bangkok 10110, Thailand;3. National Center for Genetic Engineering and Biotechnology, 113 Thailand Science Park, Khlong Luang, Pathum Thani 12120, Thailand;4. Department of Chemistry, University of Zurich, Winterthurerstrasse 190, CH-8057 Zurich, Switzerland |
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| Abstract: | The structure of a constrained bicyclic chiral derivatizing agent (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-d22, 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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| Keywords: | Constrained bicycle Chiral derivatizing agent Diels Alder reaction Deuterated molecule |
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