Preparative Organic Chemistry
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ChemInform Abstract: Formation of α-Dialkylamino Alkyllithium Intermediates in the Reaction of N,N-Dialkylamides with PhMe2SiLi Followed by a Second Lithium Reagent, and Their Alkylation, Fragmentation, Cyclization and Rearrangement by Proton Transfer.
First published: 20 June 2010
Abstract
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ChemInform Abstract
The reaction of tertiary amides, e.g. (I), with Ph-SiMe2Li and a second lithium reagent leads to α-dialkylamino alkyllithium intermediates, which undergo protonation, cf. products (III), β-elimination, cf. compound (VI), intramolecular reaction to give product (X) or intramolecular proton transfer, cf. compound (XII).
