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Development of a new bicyclic imidazole nucleophilic organocatalyst for direct enantioselective C-acylation

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Abstract

A novel chiral nucleophilic organocatalyst easily synthesized from simple starting materials bearing a 5,6,7,8-tetrahydroimidazo[1,2-a]pyridine skeleton has been developed and successfully applied in the direct enantioselective C-acylation of 3-substituted benzofuranones. Its catalytic efficiency was shown to be comparable to that of the previously reported chiral 6,7-dihydro-5H-pyrrolo[1,2-a]imidazole catalyst. A wide range of 3,3-disubstituted benzofuranones, possessing a quaternary stereocenter, were synthesized with high yields and enantioselectivities.

Graphical abstract: Development of a new bicyclic imidazole nucleophilic organocatalyst for direct enantioselective C-acylation

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Publication details

The article was received on 19 Aug 2019, accepted on 31 Oct 2019 and first published on 01 Nov 2019


Article type: Research Article
DOI: 10.1039/C9QO01025D
Org. Chem. Front., 2019, Advance Article

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    Development of a new bicyclic imidazole nucleophilic organocatalyst for direct enantioselective C-acylation

    M. Zhou, E. He, L. Zhang, J. Chen, Z. Zhang, Y. Liu and W. Zhang, Org. Chem. Front., 2019, Advance Article , DOI: 10.1039/C9QO01025D

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