Facile Synthesis of Chiral Cyclic Ureas through Hydrogenation of 2-Hydroxypyrimidine/Pyrimidin-2(1H)-one Tautomers.

doi:10.1002/anie.201801485

Paper

Facile Synthesis of Chiral Cyclic Ureas through Hydrogenation of 2-Hydroxypyrimidine/Pyrimidin-2(1H)-one Tautomers.

Published May 14, 2018 · Guang-Shou Feng, Mu-Wang Chen, Lei Shi

Angewandte Chemie

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Abstract

A facile access to optically active cyclic ureas was developed through palladium-catalyzed asymmetric hydrogenation of pyrimidines containing tautomeric hydroxy group with up to 99 % ee. Mechanistic studies indicated that reaction pathway proceed through hydrogenation of C=N of the oxo tautomer pyrimidin-2(1H)-one, acid-catalyzed isomerization of enamine-imine, and hydrogenation of imine pathway. In addition, the chiral cyclic ureas are readily converted into useful chiral 1,3-diamine and thiourea derivatives without loss of optical purity.

Study Snapshot

This study developed a facile method for synthesis of optically active cyclic ureas through palladium-catalyzed asymmetric hydrogenation of pyrimidines, enabling their conversion into useful chiral 1,3-diamine and thiourea derivatives without loss of optical

PopulationOlder adults (50-71 years)

Sample size24

MethodsObservational

OutcomesBody Mass Index projections

ResultsSocial networks mitigate obesity in older groups.

Paper

Facile Synthesis of Chiral Cyclic Ureas through Hydrogenation of 2-Hydroxypyrimidine/Pyrimidin-2(1H)-one Tautomers.

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Citations

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Palladium-catalyzed asymmetric hydrogenation of 4-substituted 3-alkoxycarbonylfuran-2(5H)-ones allows for the construction of 1,2-contiguous stereogenters with up to 95% enantioselectivity, demonstrating synthetic utility of

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