Synthesis of Unsymmetrical Polysubstituted Pyridines from β-Sulfonylvinylamines via 1-Aza-Allyl Anion Intermediates

Abstract

A modular synthesis of highly functionalized unsymmetrical pyridines has been developed from reacting β-sulfonylvinylamines with α,β-unsaturated systems in the presence of base via the formation of 1-aza-allyl anion intermediates.

β-sulfonylvinylamines - 2,4,6-triarylpyridines - 1-aza-allyl anions - α,β-unsaturated ketones - cascade reactions

References

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<A NAME="RZ92211SS-11">11</A>

Initial C-alkylation at the β-carbon of 1-aza-allyl anions is typically observed over N-alkylation; see ref. 10c.

<A NAME="RZ92211SS-12">12</A>

See Supporting Information for additional details relating to the optimization process.