期刊
ANGEWANDTE CHEMIE-INTERNATIONAL EDITION
卷 57, 期 20, 页码 5853-5857出版社
WILEY-V C H VERLAG GMBH
DOI: 10.1002/anie.201801485
关键词
1,3-diamines; cyclic ureas; palladium; pyrimidines; tautomerization
资金
- National Natural Science Foundation of China [21772195, 21532006]
- Chinese Academy of Sciences [QYZDJ-SSW-SLH035]
- Dalian Bureau of Science and Technology [2016RD07]
- strategic priority program of Chinese Academy of Sciences [XDB17020300]
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.
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