کد مقاله | کد نشریه | سال انتشار | مقاله انگلیسی | نسخه تمام متن |
---|---|---|---|---|
1314998 | 975998 | 2007 | 7 صفحه PDF | دانلود رایگان |

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.
The synthesis of a new enantiomerically pure fluorinated oxazolidinone and its use as a chiral auxiliary in Aldol condensations are described.Figure optionsDownload as PowerPoint slide
Journal: Journal of Fluorine Chemistry - Volume 128, Issue 6, June 2007, Pages 647–653