Three-Component Domino Process for the Pyrrolizine
Skeleton via [3 + 2]-Cycloaddition–Enamine Cyclization
Triggered by a Gold Catalyst
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Abstract
Pyrrolizines are
bicyclic fused azaheterocycles with a bridgehead
nitrogen contained in a core skeleton and are often found in biologically
active compounds. Despite their importance, there have been few reports
on concise and flexible syntheses of pyrrolizines. A novel one-pot,
convergent method is described for pyrrolizines by simple mixing of
iminoesters, acetylenes, and dipolarophiles in the presence of a cationic
gold catalyst and an acid additive. This domino process affords multisubstituted
pyrrolizines without handling unstable intermediates