کد مقاله | کد نشریه | سال انتشار | مقاله انگلیسی | نسخه تمام متن |
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1315628 | 976052 | 2007 | 7 صفحه PDF | دانلود رایگان |
![عکس صفحه اول مقاله: The influence of fluorine on the asymmetric reduction of fluoromethyl ketones The influence of fluorine on the asymmetric reduction of fluoromethyl ketones](/preview/png/1315628.png)
A comparative study of the asymmetric reduction of representative aryl and alkyl α-fluoro- and α-chloromethyl ketones using (−)-diisopinocampheylchloroborane [(−)-DIP-Chloride™] and (−)-B-isopinocampheyl-9-borabicyclo[3.3.1]nonane [R-Alpine-Borane®] has been made. It was observed that DIP-Chloride™ is superior in terms of the rate and enantioselectivity for both classes of halo-ketones. While the reduction of monofluoroacetone and trifluoroacetone with DIP-Chloride™ provided the product alcohols in 61% ee and 96% ee, respectively, the reduction of difluoroacetone yielded only 5% ee. The influence of a lone halogen atom was not observed for monochloroacetone, all of which point towards a chelating effect of monofluoroacetone on the Lewis acidic chloroborane.
A comparative study of the asymmetric reduction of representative aryl and alkyl α-fluoro- and α-chloromethyl ketones using (−)-diisopinocampheylchloroborane [(−)-DIP-Chloride™] and (−)-B-isopinocampheyl-9-borabicyclo[3.3.1]nonane [R-Alpine-Borane®] has been made. It was observed that DIP-Chloride™ is superior in terms of the rate and enantioselectivity for both classes of halo-ketones. While the reduction of monofluoroacetone and trifluoroacetone with DIP-Chloride™ provided the product alcohols in 61% ee and 96% ee, respectively, the reduction of difluoroacetone yielded only 5% ee. The influence of a lone halogen atom was not observed for monochloroacetone, all of which point towards a chelating effect in the presence of the Lewis acidic chloroborane.Figure optionsDownload as PowerPoint slide
Journal: Journal of Fluorine Chemistry - Volume 128, Issue 7, July 2007, Pages 844–850