A Strategy for the Synthesis of Bicyclic Fused Cyclopentenones from MBH-Carbonates of Propiolaldehydes

An effective synthetic approach has been demonstrated for the construction of diverse bicyclic fused cyclopentenones from Morita-Baylis-Hillman (MBH) carbonates of propiolaldehydes. The present transformation was initiated through the propargylation of an alkenylamine with an MBH carbonate followed by the Pauson-Khand reaction of the product methyl 3-(alkenylamino)-2-methylenealk-4-ynoate. This facile method provides diverse scaffolds of cyclopentenone fused with aza-cycles having additional functionality in good yields.

Automated summary

An effective synthetic approach for the construction of diverse bicyclic fused cyclopentenones from Morita-Baylis-Hillman (MBH) carbonates of propiolaldehydes has been demonstrated. The transformation involves the propargylation of an alkenylamine with an MBH carbonate followed by the Pauson-Khand reaction to yield cyclopentenone fused with aza-cycles having additional functionality.