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Enantioselective Synthesis of 3,4-Dihydropyrimidin-2(1H)-ones through Organocatalytic Transfer Hydrogenation of 2-Hydroxypyrimidines

Author:
Meng, Fan-Jie, Shi, Lei, Feng, Guang-Shou, Sun, Lei, Zhou, Yong-Gui
Source:
Journal of organic chemistry 2019 v.84 no.7 pp. 4435-4442
ISSN:
1520-6904
Subject:
catalytic activity, chemical structure, chemoselectivity, enantioselective synthesis, enantioselectivity, hydrogen, hydrogenation, organic chemistry, organic compounds
Abstract:
Chiral phosphoric acid-catalyzed transfer hydrogenation of 2-hydroxypyrimidines has been successfully realized using Hantzsch ester or dihydrophenanthridine as the hydrogen source, furnishing the chiral 3,4-dihydropyrimidin-2(1H)-ones (DHPMs) with excellent yields and enantioselectivities of ≤99%. Notably, a novel kind of chiral DHPMs with an alkyl stereogenic center can be prepared through highly chemoselective transfer hydrogenation.
Agid:
6362919