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Synthetic Applications of Ambiphilic C-acylimines in Organic Synthesis

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ASIAN JOURNAL OF ORGANIC CHEMISTRY
卷 11, 期 9, 页码 -

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WILEY-V C H VERLAG GMBH
DOI: 10.1002/ajoc.202200395

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C-acylimines; ambiphilic reactivity; cycloadditions; annulations; asymmetric synthesis

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C-acylimines are compounds obtained through the reaction of glyoxals and amines, which exhibit similar structures to naturally occurring substances and have unique reactivity in the synthesis of nitrogen-containing cyclic compounds. Despite the lack of available reviews in this specific area, numerous synthetic methods have been developed.
C-acylimines are generally obtained through condensation/dehydration of simple and readily available glyoxals and amines. The structure resembles naturally occurring biological substances due to the presence of the imino group (-N=C-). Chemically, C-acylimines exhibit ambiphilic reactivity, and hence, their synthetic chemistry becomes more attractive and viable for the synthesis of various aza-cyclic/heterocyclic compounds, including their asymmetric counterpart. Therefore, many synthetic methodologies were developed from these readily preparable C-acylimines. Surprisingly, there is no account/review available on this specific topic. Hence we present here an account of all the synthetic endeavours developed from C-acylimines to synthesize small molecules and complex systems using various strategies.

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