Tetrahedron p. 2035 - 2040 (1984)
Update date:2022-08-11
Topics:
Armani, E.
Dossena, A.
Marchelli, R.
Casnati, G.
Reacting aldehydes and ketones with the "ButBr-Me2SO" system produces the corresponding α-bromoderivatives 2.In the case of ketones, where more than one regioisomer is possible, bromination is obtained exclusively at the more highly substituted α-position.With slight modifications of the reaction conditions (addition of Me2S, Me2SO) it is possible to obtain "in situ" formation of either dimethyl(2-oxo-phenylalkyl)sulphonium salts 3 or of α-methylthioderivatives 4.Dimethyl(1-methyl-2-oxo-2-phenylethyl)sulphonium bromide (3h) during crystallization undergoes spontaneous resolution of the two enantiomers, as demonstrated by single crystal X-ray analysis and absolute configuration assignment.
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Doi:10.1016/j.tet.2014.07.073
(2014)Doi:10.1039/d0sc01650k
(2020)Doi:10.1016/S0014-827X(03)00113-7
(2003)Doi:10.1134/S1070363210020362
(2010)Doi:10.1002/hlca.19630460417
(1963)Doi:10.1016/S0040-4039(00)84653-5
(1986)
