Aniline-Promoted Cyclization–Replacement Cascade Reactions of 2-Hydroxycinnamaldehydes with Various Carbonic Nucleophiles through In Situ Formed N,O-Acetals

Chenguang Yu, He Huang, Xiangmin Li, Yueteng Zhang, Hao Li, Wei Wang

Research output: Contribution to journalArticlepeer-review

13 Scopus citations

Abstract

In this study, we report the harnessing of new reactivity of N,O-acetals in an aminocatalytic fashion for organic synthesis. Unlike widely used strategies requiring the use of acids and/or elevated temperatures, direct replacement of the amine component of the N,O-acetals by carbon-centered nucleophiles for C−C bond formation is realized under mild reaction conditions. Furthermore, without necessary preformation of the N,O-acetals, an amine-catalyzed in situ formation of N,O-acetals is developed. Coupling both reactions into a one-pot operation enables the achievement of a catalytic process. We demonstrate the employment of simple anilines as promoters for the cyclization–substitution cascade reactions of trans-2-hydroxycinnamaldehydes with various carbonic nucleophiles including indoles, pyrroles, naphthols, phenols, and silyl enol ethers. The process offers an alternative approach to structurally diverse, “privileged” 2-substituted 2H-chromenes. The synthetic power of the new process is furthermore shown by its application in a 2-step synthesis of the natural product candenatenin E and for the facile installation of 2-substituted 2H-chromene moieties into biologically active indoles.

Original languageEnglish (US)
Pages (from-to)9240-9246
Number of pages7
JournalChemistry - A European Journal
Volume22
Issue number27
DOIs
StatePublished - Jun 27 2016
Externally publishedYes

Keywords

  • N,O-acetals
  • aminocatalysis
  • cascade reactions
  • chromenes
  • iminium ions

ASJC Scopus subject areas

  • Catalysis
  • Organic Chemistry

Fingerprint

Dive into the research topics of 'Aniline-Promoted Cyclization–Replacement Cascade Reactions of 2-Hydroxycinnamaldehydes with Various Carbonic Nucleophiles through In Situ Formed N,O-Acetals'. Together they form a unique fingerprint.

Cite this