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Feng GS, Chen MW, Shi L, et al. Facile Synthesis of Chiral Cyclic Ureas through Hydrogenation of 2-Hydroxypyrimidine/Pyrimidin-2(1H)-one Tautomers. Angew Chem Int Ed Engl. 2018;57(20):5853-5857doi: 10.1002/anie.201801485.
Feng, G. S., Chen, M. W., Shi, L., & Zhou, Y. G. (2018). Facile Synthesis of Chiral Cyclic Ureas through Hydrogenation of 2-Hydroxypyrimidine/Pyrimidin-2(1H)-one Tautomers. Angewandte Chemie (International ed. in English), 57(20), 5853-5857. https://doi.org/10.1002/anie.201801485
Feng, Guang-Shou, et al. "Facile Synthesis of Chiral Cyclic Ureas through Hydrogenation of 2-Hydroxypyrimidine/Pyrimidin-2(1H)-one Tautomers." Angewandte Chemie (International ed. in English) vol. 57,20 (2018): 5853-5857. doi: https://doi.org/10.1002/anie.201801485
Feng GS, Chen MW, Shi L, Zhou YG. Facile Synthesis of Chiral Cyclic Ureas through Hydrogenation of 2-Hydroxypyrimidine/Pyrimidin-2(1H)-one Tautomers. Angew Chem Int Ed Engl. 2018 May 14;57(20):5853-5857. doi: 10.1002/anie.201801485. Epub 2018 Apr 17. PMID: 29575705.
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Angew Chem Int Ed Engl. 2018 May 14;57(20):5853-5857. doi: 10.1002/anie.201801485. Epub 2018 Apr 17.

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

Angewandte Chemie (International ed. in English)

Guang-Shou Feng, Mu-Wang Chen, Lei Shi, Yong-Gui Zhou

Affiliations

  1. State Key Laboratory of Catalysis, Dalian Institute of Chemical Physics, Chinese Academy of Sciences, Dalian, 116023, China.
  2. University of Chinese Academy of Sciences, Beijing, 100049, China.

PMID: 29575705 DOI: 10.1002/anie.201801485

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.

© 2018 Wiley-VCH Verlag GmbH & Co. KGaA, Weinheim.

Keywords: 1,3-diamines; cyclic ureas; palladium; pyrimidines; tautomerization

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