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Microwave-Assisted Solvent-Free Synthesis of Enantiomerically Pure <i>N</i>-(<i>tert</i>-Butylsulfinyl)imines
A simple, environmentally friendly, and very efficient
procedure
for the synthesis of optically pure <i>N</i>-(<i>tert</i>-butylsulfinyl)imines has been developed with microwave-promoted
condensation of aldehydes and ketones using (<i>R</i>)-2-methylpropane-2-sulfinamide
in the presence of Ti(OEt)<sub>4</sub>, under solvent-free conditions.
This procedure allows for the preparation of a variety of sulfinyl
aldimines with excellent yields and purities in only 10 min, making
any further purification of the imines unnecessary. Several sulfinyl
ketimines have also been prepared in good yields by extension of the
reaction times to 1 h. This methodology has proved to be equally efficient
for the synthesis of aromatic, heteroaromatic, and aliphatic <i>N</i>-(<i>tert</i>-butylsulfinyl)imines. Conventional
heating has also been shown to be useful to promote these reactions,
especially for the synthesis of aldimines