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Enantioselective 1,4‐Reduction of Pyrimidin‐2‐ones to Synthesize Novel 3,4‐Dihydropyrimidin‐2(1 H )‐ones Containing an Alkyl‐substituted Stereogenic Center
Author(s) -
Meng FanJie,
Shi Lei,
Jiang WenFeng,
Lu XiaoBing
Publication year - 2020
Publication title -
asian journal of organic chemistry
Language(s) - English
Resource type - Journals
SCImago Journal Rank - 0.846
H-Index - 44
eISSN - 2193-5815
pISSN - 2193-5807
DOI - 10.1002/ajoc.202000100
Subject(s) - stereocenter , chemistry , enantioselective synthesis , phosphoric acid , alkyl , center (category theory) , combinatorial chemistry , reduction (mathematics) , chirality (physics) , stereochemistry , organic chemistry , catalysis , mathematics , crystallography , chiral symmetry breaking , geometry , physics , quantum mechanics , quark , nambu–jona lasinio model
An efficient asymmetric 1,4‐reduction of pyrimidin‐2‐ones with a chiral phosphoric acid‐catalyzed system has been successfully developed, furnishing a series of chiral 3,4‐dihydro‐pyrimidin‐2‐one derivatives in excellent yields and enantioselectivities (up to 99% ee). Notably, this methodology enables a novel kind of chiral 3,4‐dihydropyrimidin‐2‐one with an alkyl stereogenic center to be prepared in high optical purity for the first time.