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Chiral Spirocyclic Phosphoric Acid‐Catalyzed Synthesis of 4‐Alkyl‐3,4‐dihydropyrimidin‐2(1H)‐one Derivatives by Asymmetric Biginelli Reactions
Author(s) -
Guo Yongbiao,
Gao Zhenhua,
Wang Kang,
Li Junchen,
Bi Xiaojing,
Guo Lei,
Liu Haibo,
Shi Enxue,
Xiao Junhua
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.201900718
Subject(s) - chemistry , biginelli reaction , alkyl , phosphoric acid , yield (engineering) , catalysis , organic chemistry , combinatorial chemistry , materials science , metallurgy
A chiral spirocyclic phosphoric acid‐catalyzed asymmetric Biginelli reaction based on aliphatic aldehydes has been realized for the synthesis of biologically important and synthetically useful 4‐alkyl‐3,4‐dihydropyrimidin‐2‐(1H)‐one (4‐alkyl−DHPM) skeletons in good yield and with high levels of enantioinduction. The utility of this transformation was further demonstrated by direct thionation and C−C/C−N bond construction to provide a series of 4‐alkyl−DHPMs derivatives without any loss of optical activity, providing streamlined access to the formal synthesis of Batzelladine A.