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

H Matsubara, L Maeda, H Sugiyama, I Ryu

Index: Matsubara, Hiroshi; Maeda, Louis; Sugiyama, Hiroyuki; Ryu, Ilhyong Synthesis, 2007 , # 18 p. 2901 - 2912

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Citation Number: 7

Abstract

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 ...