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Stereodivergent Palladium- and Rhodium-Catalyzed Intramolecular Addition of Tosylureas to Allenes: Diastereoselective Synthesis of Tetrahydropyrimidinones.

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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.

Keywords: rhodium; intramolecular addition; palladium rhodium; tosylureas allenes; palladium; addition tosylureas

Journal Title: Organic letters
Year Published: 2021

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