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Iridium-Catalyzed Asymmetric Hydrogenation of 4,6-Disubstituted 2-Hydroxypyrimidines

Author:
Feng, Guang-Shou, Shi, Lei, Meng, Fan-Jie, Chen, Mu-Wang, Zhou, Yong-Gui
Source:
Organic letters 2018 v.20 no.20 pp. 6415-6419
ISSN:
1523-7052
Subject:
chemical structure, diastereoselectivity, enantioselectivity, hydrogen, hydrogenation, organic compounds, tautomerization
Abstract:
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.
Agid:
6166864