Synthesis of a new fluorinated oxazolidinone and its reactivity as a chiral auxiliary in Aldol reactions

A new enantiomerically pure fluorinated oxazolidinone has been prepared from a fluorinated imidoyl chloride and an optically pure sulfoxide. The diastereoselective reduction of the β-iminosulfoxide thus formed followed by elimination of the sulfoxide and cyclization of the created aminoalcohol furnishes the desired product. The fluorinated oxazolidinone was subsequently used as a chiral auxiliary in Aldol reactions. We also found that the selective formation of the syn-Evans and syn-non-Evans diastereoisomer can be controlled by adjusting the Lewis acid/base ratio.

Graphical abstractThe synthesis of a new enantiomerically pure fluorinated oxazolidinone and its use as a chiral auxiliary in Aldol condensations are described.Figure optionsDownload full-size imageDownload as PowerPoint slide