Salts of Mosher's thioacid: agents for determining the enantiomer excess of SN2 substrates
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.
Richman, Jack E.
supporting information; experimental part
p. 2793 - 2796
(2010/07/06)
Thioacids and thioacid salts for determining the enantiomeric excess of chiral compounds containing an electrophilic carbon center
The invention provides novel chiral compounds including 2-methoxy-2-trifluoromethylphenylacetic thioacid useful to react with and analyze other chiral compounds that have an electrophilic chiral carbon center.
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Page/Page column 19-20
(2010/07/02)
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