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

Arne G. A. Geissler, Jasmin R. Riesterer and Bernhard Breit*

*Institute of Organic Chemistry, Albert-Ludwigs-Universitšt Freiburg, Albertstr. 21, 79104 Freiburg, Germany, Email: bernhard.breitchemie.uni-freiburg.de

A. G. A. Geissler, K. R. Riesterer, B. Breit, Org. Lett., 2021, 23, 9168-9172.

DOI: 10.1021/acs.orglett.1c03482


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Abstract

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 in excellent yields. The obtained tetrahydropyrimidinones are easily deprotected and modified.

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Key Words

1,3-diamines, allylic amines, N-heterocycles


ID: J54-Y2021