期刊
ORGANIC LETTERS
卷 20, 期 20, 页码 6415-6419出版社
AMER CHEMICAL SOC
DOI: 10.1021/acs.orglett.8b02723
关键词
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资金
- National Natural Science Foundation of China [21772195, 21532006]
- Chinese Academy of Sciences [QYZDJ-SSW-SLH035]
- Dalian Bureau of Science and Technology [2016RD07]
An efficient iridium-catalyzed hydrogenation of 4,6-disubstituted 2-hydroxypyrimidines has been achieved, giving chiral cyclic ureas with excellent diastereoselectivities and up to 96% ee of enantioselectivities. In the presence of the in situ generated hydrogen halide, the equilibrium of the lactame-lactime tautomerism of 2-hydroxypyrimidine is more toward the oxo form with lower aromaticity, which effectively improves the reactivity to facilitate hydrogenation. Moreover, the cyclic ureas could be readily converted into chiral 1,3-diamine derivatives without loss of optical purity.
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