Doubly vinylogous and doubly rearomative functionalization of 2-alkyl-3-furfurals

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Abstract
The manuscript describes a straightforward functionalization of 2-alkyl-3-furfurals via simple aminocatalytic conjugate addition. The reaction proceeds through the formation of dearomatized dienamine-like intermediate that undergoes 1,6-addition to 4-alkylidene-2,6-dialkylcyclohexa-2,5-dienones. This process can be described as doubly rearomative as it proceeds with the re-formation of both furan and phenyl aromatic moieties. Target products have been obtained in a highly stereoselective manner, providing an interesting example of 2-alkyl-3-furfural functionalization via doubly vinylogous Michael addition. The mechanism of the reaction has been studied by means of computational methods.
Funding Information
  • Narodowe Centrum Nauki (UMO-2018/30/Q/ST5/00466)
  • National Natural Science Foundation of China (21961132004)

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