Domino formation of enamines--intramolecular cyclizations to 1-aminotetralins from γ-arylallene aldehydes and amines.

Org Lett

Centre de Recherche de Gif, Institut de Chimie des Substances Naturelles, CNRS, 1 Avenue de la Terrasse, 91198 Gif-sur-Yvette, France.

Published: October 2014

1,5-/1,6-Allenals conjugated to an aromatic ring undergo a cyclization, in the presence of an amine, that leads to tricyclic compounds including the 1-aminotetralin scaffold. This domino process combines the in situ formation of the enamine and the cyclization affording the tricyclic 1-aminotetralins in very high diastereoselectivities.

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Source
http://dx.doi.org/10.1021/ol5026712DOI Listing

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