Salts of Mosher's thioacid: agents for determining the enantiomer excess of SN2 substrates

Jack E. Richman

doi:10.1016/j.tetlet.2010.03.041

Salts of Mosher's thioacid: agents for determining the enantiomer excess of S_N2 substrates

Jack E. Richman

Biotechnology Institute

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

4 Scopus citations

Abstract

The racemic and the (S)-enantiomer of Mosher's thioacid, 2-methoxy-2-trifluoromethylphenylacetic thioacid, form air-stable salts with Proton Sponge [1,8-bis(dimethylamino)naphthalene]. These salts are powerful nucleophiles that react cleanly (S_N2 inversion) in CDCl₃ with optically active alkyl halides ranging in reactivities from unactivated alkyl bromides and iodides to benzylic bromides. The diastereomeric excess (de) of the thioester products indicates the enantiomeric excess (ee) of the starting alkyl halides.

Original language	English (US)
Pages (from-to)	2793-2796
Number of pages	4
Journal	Tetrahedron Letters
Volume	51
Issue number	21
DOIs	https://doi.org/10.1016/j.tetlet.2010.03.041
State	Published - May 26 2010

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abstract = "The racemic and the (S)-enantiomer of Mosher's thioacid, 2-methoxy-2-trifluoromethylphenylacetic thioacid, form air-stable salts with Proton Sponge [1,8-bis(dimethylamino)naphthalene]. These salts are powerful nucleophiles that react cleanly (SN2 inversion) in CDCl3 with optically active alkyl halides ranging in reactivities from unactivated alkyl bromides and iodides to benzylic bromides. The diastereomeric excess (de) of the thioester products indicates the enantiomeric excess (ee) of the starting alkyl halides.",

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N2 - The racemic and the (S)-enantiomer of Mosher's thioacid, 2-methoxy-2-trifluoromethylphenylacetic thioacid, form air-stable salts with Proton Sponge [1,8-bis(dimethylamino)naphthalene]. These salts are powerful nucleophiles that react cleanly (SN2 inversion) in CDCl3 with optically active alkyl halides ranging in reactivities from unactivated alkyl bromides and iodides to benzylic bromides. The diastereomeric excess (de) of the thioester products indicates the enantiomeric excess (ee) of the starting alkyl halides.

AB - The racemic and the (S)-enantiomer of Mosher's thioacid, 2-methoxy-2-trifluoromethylphenylacetic thioacid, form air-stable salts with Proton Sponge [1,8-bis(dimethylamino)naphthalene]. These salts are powerful nucleophiles that react cleanly (SN2 inversion) in CDCl3 with optically active alkyl halides ranging in reactivities from unactivated alkyl bromides and iodides to benzylic bromides. The diastereomeric excess (de) of the thioester products indicates the enantiomeric excess (ee) of the starting alkyl halides.

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Salts of Mosher's thioacid: agents for determining the enantiomer excess of S_N2 substrates

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