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

Jakapun Soponpong; Kulvadee Dolsophon; Chawanee Thongpanchang; Anthony Linden; Tienthong Thongpanchang

doi:10.1016/j.tetlet.2019.01.013

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

Jakapun Soponpong
, Kulvadee Dolsophon
, Chawanee Thongpanchang
, Anthony Linden
, Tienthong Thongpanchang

Mahidol University
Srinakharinwirot University
National Science and Technology Development Agency (NSTDA)
University of Zürich

Research output: Contribution to journal › Article › peer-review

5 Citations (Scopus)

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-d ₂ 2, 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 ¹ H NMR spectra of THENA-d ₂ derivatives is less complicated and the new CDA thus offers simpler NMR spectra for data interpretation.

Original language	English
Pages (from-to)	497-500
Number of pages	4
Journal	Tetrahedron Letters
Volume	60
Issue number	6
DOIs	https://doi.org/10.1016/j.tetlet.2019.01.013
Publication status	Published - 7 Feb 2019
Externally published	Yes

Keywords

Chiral derivatizing agent
Constrained bicycle
Deuterated molecule
Diels Alder reaction

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10.1016/j.tetlet.2019.01.013

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title = "Application of deuterated THENA for assigning the absolute configuration of chiral secondary alcohols",

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-d 2 2, 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 1 H NMR spectra of THENA-d 2 derivatives is less complicated and the new CDA thus offers simpler NMR spectra for data interpretation.",

keywords = "Chiral derivatizing agent, Constrained bicycle, Deuterated molecule, Diels Alder reaction",

author = "Jakapun Soponpong and Kulvadee Dolsophon and Chawanee Thongpanchang and Anthony Linden and Tienthong Thongpanchang",

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T1 - Application of deuterated THENA for assigning the absolute configuration of chiral secondary alcohols

AU - Soponpong, Jakapun

AU - Dolsophon, Kulvadee

AU - Thongpanchang, Chawanee

AU - Linden, Anthony

AU - Thongpanchang, Tienthong

PY - 2019/2/7

Y1 - 2019/2/7

N2 - 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-d 2 2, 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 1 H NMR spectra of THENA-d 2 derivatives is less complicated and the new CDA thus offers simpler NMR spectra for data interpretation.

AB - 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-d 2 2, 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 1 H NMR spectra of THENA-d 2 derivatives is less complicated and the new CDA thus offers simpler NMR spectra for data interpretation.

KW - Chiral derivatizing agent

KW - Constrained bicycle

KW - Deuterated molecule

KW - Diels Alder reaction

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DO - 10.1016/j.tetlet.2019.01.013

M3 - Article

AN - SCOPUS:85059805363

SN - 0040-4039

VL - 60

SP - 497

EP - 500

JO - Tetrahedron Letters

JF - Tetrahedron Letters

IS - 6

ER -

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

Abstract

Keywords

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