Gold(I)‐Catalyzed Domino Reaction: An Access to Furooxepines

Abstract

Abstract. We report herein the synthesis of [7,5]‐fused bicyclic acetals, also named furooxepines through a gold(I)‐catalyzed domino reaction. During this transformation, two molecules of homopropargyl alcohol react together, in a sequence including an intramolecular hydroalkoxylation, condensation, a 1,6‐enyne cycloisomerization, acetalization and an isomerization. This gold(I)‐catalyzed domino reaction allow the formation of three bonds, two heterocycles and a tetrasubstituted carbon stereocenters in a one‐step operation with 100% atom economy. Post‐functionalizations allow the formation of tetrahydrofurans.

Development of 3-triazenylaryne and its application to iterative aryne reactions via o-triazenylarylboronic acids

“…The oxygen atom of 7c or 8ca will participate in the selective transformation of the alkyne moiety. 14 The cycloaddition of 2a′ with N -phenylpyrrole ( 4f ) afforded 8af in 59% yield. The reaction with azide 4g or amine 4h led to the formation of a regioisomeric mixture of 8ag and 8ag′ ( 8ag : 8ag′ = 55 : 45) or 8ah and 8ah′ ( 8ah : 8ah′ = 72 : 28).…”