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Updated: Jan 20, 2026

A Protocol for Safe Lithiation Reactions Using Organolithium Reagents
Published on: November 12, 2016
Enantioselective Alkylation of 2-Alkylpyridines Controlled by Organolithium Aggregation
Joshua J Gladfelder1, Santanu Ghosh1, Maša Podunavac1
1Department of Chemistry and Biochemistry , University of California, Santa Barbara , Santa Barbara , California 93106 , United States.
Abstract:
Direct enantioselective α-alkylation of 2-alkylpyridines provides access to chiral pyridines via an operationally simple protocol that obviates the need for prefunctionalization or preactivation of the substrate. The alkylation is accomplished using chiral lithium amides as noncovalent stereodirecting auxiliaries. Crystallographic and solution NMR studies provide insight into the structure of well-defined chiral aggregates in which a lithium amide reagent directs asymmetric alkylation.
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