α-Functionalization of Cyclic Secondary Amines: Lewis Acid Promoted Addition of Organometallics to Transient Imines
Cyclic imines, generated in situ from their corresponding N-lithiated amines and a ketone hydride acceptor, undergo reactions with a range of organometallic nucleophiles to generate α-functionalized amines in a single operation. Activation of the transient imines by Lewis acids that are compatible with the presence of lithium alkoxides was found to be crucial to accommodate a broad range of nucleophiles including lithium acetylides, Grignard reagents, and aryllithiums with attenuated reactivities.
Paul, Anirudra,Seidel, Daniel
supporting information
p. 8778 - 8782
(2019/06/07)
A NOVEL THREE CARBON-AMINO GRIGNARD REAGENT: ITS USE IN AN EFFICIENT PYRROLIDINE SYNTHESIS
A novel primary amino protected Grignard reagent has been developed; 2,2,5,5-tetramethyl-1-aza-2,5-disilacyclopentane-1-propyl magnesium bromide 1a.Its usefulness is illustrated in the synthesis of 2-substituted pyrrolidines.
Basha, Fatima Z.,DeBernardis, John F.
p. 5271 - 5274
(2007/10/02)
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