A Simple Determination Method of the Absolute Configuration of 1-Arylethanthiols by an Intramolecular CH/π Shielding Effect in 1H-NMR of Diastereomeric Thiol Esters

Masato Matsugi; Yuri Hagimoto; Kinuyo Itoh; Masatomo Nojima; Yasuyuki Kita

doi:10.1248/cpb.51.460

Chemical and Pharmaceutical Bulletin

Online ISSN : 1347-5223
Print ISSN : 0009-2363

Notes

A Simple Determination Method of the Absolute Configuration of 1-Arylethanthiols by an Intramolecular CH/π Shielding Effect in ¹H-NMR of Diastereomeric Thiol Esters

Masato Matsugi, Yuri Hagimoto, Kinuyo Itoh, Masatomo Nojima, Yasuyuki Kita

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Keywords: thiol, absolute configuration, ¹H-NMR, diastereomer

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Volume 51 (2003) Issue 4 Pages 460-462

DOI https://doi.org/10.1248/cpb.51.460

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Abstract

A simple method for the determination of the absolute configuration of 1-arylethanthiols was achieved by the observation of an intramolecular CH/π shielding effect in ¹H-NMR of the corresponding thiol esters. (S)-Isomer of the diastereomers always shows remarkable shielding effect.

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