Stereospecific Intramolecular Arylation of 2- and
3‑Pyridyl Substituted Alkylamines via Configurationally Stable
α‑Pyridyl Organolithiums
Posted on 2017-01-18 - 17:52
Treatment of N′-aryl
urea derivatives of
enantiomerically enriched α-(2-pyridyl) and α-(3-pyridyl)alkylamines
with a base leads to the migration of the N′-aryl
substituent from N to C in a ‘nonclassical’ intramolecular
nucleophilic aromatic substitution reaction. Both electron-rich and
-poor rings migrate successfully. A new quaternary stereogenic center
is formed adjacent to the pyridine ring with high stereospecificity,
even when the intermediate anion is a presumably planar 2-picolyllithium.
Base hydrolysis of the urea gives enantiomerically enriched α-pyridylalkylamines.
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Maury, Julien; Zawodny, Wojciech; Clayden, Jonathan (2017). Stereospecific Intramolecular Arylation of 2- and
3‑Pyridyl Substituted Alkylamines via Configurationally Stable
α‑Pyridyl Organolithiums. ACS Publications. Collection. https://doi.org/10.1021/acs.orglett.6b03603
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AUTHORS (3)
JM
Julien Maury
WZ
Wojciech Zawodny
JC
Jonathan Clayden
KEYWORDS
2- picolyllithiumderivativeα- pyridylalkylaminesStableAlkylamineenantiomericallyquaternary stereogenic centerConfigurationallyOrganolithiumSubstitutedStereospecific Intramolecular ArylationstereospecificityureaPyridylnonclassicalbase hydrolysisanionsubstituentnucleophilicsubstitution reactionarylelectron-richintramolecularpyridine ringmigration