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Synthesis 2007(18): 2901-2912
DOI: 10.1055/s-2007-983877
DOI: 10.1055/s-2007-983877
FEATUREARTICLE
© Georg Thieme Verlag Stuttgart · New York
Chiral and Achiral Lithium Amides Having a Fluorous Ponytail: Preparation and Evaluation as a Recycling Reagent for Lithium Enolate Generation
Further Information
Received
4 June 2007
Publication Date:
29 August 2007 (online)
Publication History
Publication Date:
29 August 2007 (online)
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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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References
These structures were optimized by MMMF using Spartan 04 with freezing geometries around lithium.