Organic Letters 2014-10-17

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

Valérian Gobé, Pascal Retailleau, Xavier Guinchard

Index: Org. Lett. 16(20) , 5438-41, (2014)

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Abstract

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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