کد مقاله | کد نشریه | سال انتشار | مقاله انگلیسی | نسخه تمام متن |
---|---|---|---|---|
1313699 | 1499356 | 2012 | 6 صفحه PDF | دانلود رایگان |
![عکس صفحه اول مقاله: The Regio-specific solvent controlled asymmetric Strecker reaction of trifluoromethyl α,β-unsaturated N-tert-butanesulfinyl ketimines with trimethylsilyl cyanide The Regio-specific solvent controlled asymmetric Strecker reaction of trifluoromethyl α,β-unsaturated N-tert-butanesulfinyl ketimines with trimethylsilyl cyanide](/preview/png/1313699.png)
The stereoselectivity of the reaction of (Rs)-trifluoromethyl α,β-unsaturated N-tert-butanesulfinyl ketimines with TMSCN was studied. The diastereomers of α-trifluoromethyl unsaturated cyano amines were obtained, respectively, in good yields with excellent diastereoselectivities in terms of the different solvents used. In c-hexane, the (S, Rs)-isomer was obtained with up to 17:1 dr, whereas the (R, Rs)-isomer was generated as the main product with up to 145:1 dr in DMF at −60 °C.
The stereoselectivity of the reaction of (Rs)-trifluoromethyl α,β-unsaturated N-tert-butanesulfinyl ketimines with TMSCN was studied. The diastereomers of α-trifluoromethyl unsaturated cyano amines were obtained, respectively, in good yields with excellent diastereoselectivities in terms of the different solvents used. In c-hexane, the (S, Rs)-isomer was obtained with up to 17:1 dr, whereas the (R, Rs)-isomer was generated as the main product with up to 145:1 dr in DMF at −60 °C.Figure optionsDownload as PowerPoint slideHighlights
► The reaction of chiral N-tert-butanesulfinyl ketimines with TMSCN was studied.
► Different diastereoselectivities were obtained in terms of the solvents used.
► In c-hexane, d.r. (2a:3a) of the addition products is up to 1:17.
► In DMF, a reversed diastereoselectivity was observed with up to 145:1 d.r. (2a:3a).
Journal: Journal of Fluorine Chemistry - Volume 144, December 2012, Pages 102–107