Journal
JOURNAL OF THE AMERICAN CHEMICAL SOCIETY
Volume 141, Issue 38, Pages 15024-15028Publisher
AMER CHEMICAL SOC
DOI: 10.1021/jacs.9b08659
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Funding
- National Science Foundation [CHE 1361654]
- NIH (NIGMS) [R01-077379, R01-131713]
- SERB
- IUSSTF
- Mellichamp Academic Initiative in Sustainability at UCSB
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Direct enantioselective alpha-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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