Palladium-Catalyzed [4 + 2] Cycloaddition of Aldimines
and 1,4-Dipolar Equivalents via Amphiphilic Allylation
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Abstract
The
combination of Pd catalyst and diethylzinc with triethylborane
promotes the amphiphilic allylation of aldimines with 2,3-bismethylenebutane-1,4-diol
derivatives to serve as bis-allylic zwitterion species to form 3,4-bismethylenepiperidines
via a formal [4 + 2] cycloaddition reaction. 3,4-Bismethylenepiperidine
rings are applicable for the synthesis of isoquinoline derivatives
via the Diels–Alder reaction followed by an oxidation reaction
with DDQ