Journal
CHEMISTRY-A EUROPEAN JOURNAL
Volume 22, Issue 27, Pages 9240-9246Publisher
WILEY-V C H VERLAG GMBH
DOI: 10.1002/chem.201601112
Keywords
aminocatalysis; cascade reactions; chromenes; iminium ions; N,O-acetals
Categories
Funding
- NSF [CHE-1565085]
- National Science Foundation of China [21372073]
- Division Of Chemistry
- Direct For Mathematical & Physical Scien [1565085] Funding Source: National Science Foundation
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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.
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