Elusive 2-aminofuran Diels–Alder substrates for a straightforward synthesis of polysubstituted anilines?

Organic & Biomolecular Chemistry Pub Date: 2013-08-02 DOI: 10.1039/C3OB41411F

Abstract

The first multicomponent coupling of isocyanides, α,β-unsaturated carbonylic compounds and dienophiles, based on the trapping of unstable intermediate 2-aminofurans, is described. This novel tandem [4 + 1]–[4 + 2] cycloaddition is efficiently catalysed by yttrium triflate and constitutes an operationally simple and highly convergent approach to a variety of polysubstituted anilines. Moreover, this methodology permits the use of tert-butylisocyanide as a convertible isocyanide to yield directly N-unprotected anilines in the same pot.

Graphical abstract: Elusive 2-aminofuran Diels–Alder substrates for a straightforward synthesis of polysubstituted anilines
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