Chemoselective Intramolecular
Alkylation of the Blaise
Reaction Intermediates: Tandem One-Pot Synthesis of <i>exo</i>-Cyclic Enaminoesters and Their Applications toward the Synthesis
of <i>N</i>-Heterocyclic Compounds
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Abstract
The intramolecular alkylative reactivity and N/C selectivity
of
the various Blaise reaction intermediates, which are formed from the
reaction of the Reformatsky reagents with ω-chloroalkyl nitriles,
did not reach the synthetic potential as an entry to <i>exo</i>-cyclic enaminoesters. To circumvent this issue, various additives
were investigated, among which the addition of NaHMDS dramatically
enhanced the reactivity and N/C selectivity. This modification provided
a highly efficient route for the synthesis of various <i>N</i>-fused heterocyclic compounds, as it requires only two steps from
nitriles