“…Inspired by this, we envisioned that the nucleophilic attack by carboxylic acids on VECs might provide a stereocontrolled method for the construction of multisubstituted allylic esters with a naked allyl alcohol moiety. Such complex structures are fundamental building blocks in many bioactive natural products and pharmaceutically relevant compounds, such as 19-nor-neo-clerodane (Figure 1A), 7 cytotoxic vernolide (Figure 1B), 8 sesquiterpene lactone (Figure 1C), 9 and juniferol ester (Figure 1D). 10 Given the presence of α,β-unsaturated carbonyl structures in these important molecules, we recently wondered whether it might be possible to combine the ring-opening of cyclopropenones with the decarboxylation of vinylethylene carbonates to access a vast array of synthetically valuable scaffolds in domino reactions.…”
A novel Pd-catalyzed three-component domino reaction
for the stereoselective
synthesis of highly functionalized allyl cinnamates has been developed.
In this protocol, a sequential process of C–C bond activation
and intermolecular allylic substitution was well-organized. The key
for this transformation is the in situ generated
hydrolysis product of cyclopropenone, which triggered a new reaction
with vinylethylene carbonates. The reaction mechanism was investigated,
demonstrating the high stereoselectivity and excellent atomic economy
in this process.
“…Inspired by this, we envisioned that the nucleophilic attack by carboxylic acids on VECs might provide a stereocontrolled method for the construction of multisubstituted allylic esters with a naked allyl alcohol moiety. Such complex structures are fundamental building blocks in many bioactive natural products and pharmaceutically relevant compounds, such as 19-nor-neo-clerodane (Figure 1A), 7 cytotoxic vernolide (Figure 1B), 8 sesquiterpene lactone (Figure 1C), 9 and juniferol ester (Figure 1D). 10 Given the presence of α,β-unsaturated carbonyl structures in these important molecules, we recently wondered whether it might be possible to combine the ring-opening of cyclopropenones with the decarboxylation of vinylethylene carbonates to access a vast array of synthetically valuable scaffolds in domino reactions.…”
A novel Pd-catalyzed three-component domino reaction
for the stereoselective
synthesis of highly functionalized allyl cinnamates has been developed.
In this protocol, a sequential process of C–C bond activation
and intermolecular allylic substitution was well-organized. The key
for this transformation is the in situ generated
hydrolysis product of cyclopropenone, which triggered a new reaction
with vinylethylene carbonates. The reaction mechanism was investigated,
demonstrating the high stereoselectivity and excellent atomic economy
in this process.
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