The intramolecular addition of tosylureas to allenes is highly syn-/anti-diastereoselective when employing a palladium or rhodium-based catalytic system and affords 1,3-cyclic ureas. Under palladium catalysis a range of thermodynamic anti-tetrahydropyrimidinones… Click to show full abstract
The intramolecular addition of tosylureas to allenes is highly syn-/anti-diastereoselective when employing a palladium or rhodium-based catalytic system and affords 1,3-cyclic ureas. Under palladium catalysis a range of thermodynamic anti-tetrahydropyrimidinones are accessible, while rhodium catalysis allows synthesis of the kinetic syn-tetrahydropyrimidinones. For a representative scope of substrates both cyclic ureas were obtained in excellent yields and diastereoselectivities. The obtained tetrahydropyrimidinones were shown to be easily deprotected and modified to demonstrate the synthetic value.
               
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