Asymmetric synthesis of chiral tricyclic 3,4-dihydropyrimidin-2-thione derivatives catalyzed by chiral imidodiphosphoric acid

The asymmetric synthesis of 3,4-dihydropyrimidin-2-(1 H )-one thioacetals was achieved for the first time using a chiral imidodiphosphoric acid catalyst. The Biginelli reaction involving aromatic aldehydes, thiourea, and 1,3-cyclohexanedione as a multi-component reaction was conducted in ethyl aceta...

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Bibliographic Details
Published in:New journal of chemistry 2024-09, Vol.48 (36), p.15943-15947
Main Authors: Kong, Lingkai, Wang, Peng, Ju, Chunzhi, Zhang, Guangliang, Zhang, Suoqin
Format: Article
Language:English
Subjects:
Aldehydes
Asymmetry
Catalysts
Chemical synthesis
Enantiomers
Ethyl acetate
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Summary:The asymmetric synthesis of 3,4-dihydropyrimidin-2-(1 H )-one thioacetals was achieved for the first time using a chiral imidodiphosphoric acid catalyst. The Biginelli reaction involving aromatic aldehydes, thiourea, and 1,3-cyclohexanedione as a multi-component reaction was conducted in ethyl acetate at 40 °C with a chiral imidodiphosphoric acid catalyst. Under mild conditions, a series of chiral polycyclic 3,4-dihydropyrimidin-2-(1 H )-one thioacetals were obtained with high yields and excellent enantioselectivity (up to 99% ee). The asymmetric synthesis of 3,4-dihydropyrimidin-2-(1 H )-one thioacetals was achieved for the first time using a chiral imidodiphosphoric acid catalyst.
ISSN:1144-0546
1369-9261
DOI:10.1039/d4nj03039g