Chiral and achiral lithium amides having a fluorous ponytail: Preparation and evaluation as a recycling reagent for lithium enolate generation

Hiroshi Matsubara*, Louis Maeda, Hiroyuki Sugiyama, Ilhyong Ryu

*Corresponding author for this work

研究成果: Article同行評審

11 引文 斯高帕斯(Scopus)

摘要

Diisopropylamine derivatives bearing a perfluoroalkyl chain were prepared and converted to the corresponding lithium amides by treatment with n-butyllithium. The fluorous lithium amides reacted with ketones to efficiently produce lithium enolates. Asymmetric deprotonation of prochiral ketones was also studied using lithium amides derived from chiral fluorous amines, which gave optical yields comparable with the parent nonfluorous chiral lithium amides. These reusable fluorous amines can be easily recovered by liquid-liquid extraction or chromatographic separation.

原文English
頁(從 - 到)2901-2912
頁數12
期刊Synthesis
發行號18
DOIs
出版狀態Published - 17 九月 2007

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