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

doi:10.1055/s-2007-983877

FEATUREARTICLE

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*
Department of Chemistry, Graduate School of Science, Osaka Prefecture University, Sakai, Osaka 599-8531, Japan
Fax: +81(72)2549695; e-Mail: ryu@c.s.osakafu-u.ac.jp;

Abstract

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Abstract

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.

Key words

fluorous - chiral amine - enolate - LDA - asymmetric deprotonation - recycling

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Referenzen

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