Front Cover: Gold(I)‐Catalysed Hydroarylation of Lactam‐Derived Enynes as an Entry to Tetrahydrobenzo[g]quinolines (Eur. J. Org. Chem. 6/2020)

Abstract

The Front Cover shows a chemist picking a fruit from a tree with his golden glove. The fruit represents tetrahydrobenzo[g]quinolines, and the chemist is going to add it to other fruits he has already collected from the δ‐valerolactam tree. Indeed, the gold‐catalysed synthesis of tetrahydrobenzo[g]quinolines enlarges the palette of molecular scaffolds accessible in few steps from the same simple lactam precursor. The authors acknowledge Federico Sini for graphical support. More information can be found in the Full Paper by C. Prandi et al.

Gold(I)‐Catalysed Hydroarylation of Lactam‐Derived Enynes as an Entry to Tetrahydrobenzo[g]quinolines

“…The gold-activated triple bond of the lactam-derived enyne can be reacted intramolecularly with nucleophiles either part of the protecting group on nitrogen (Scheme 1, path 1), [13] or on the side chain (path 2), [14] or alternatively with external nucleophiles (path 3). [15] catalysed reaction is carried out with (C 6 F 5 ) 3 PAuCl/AgNTf 2 as the catalyst system and proceeds via a 6-exo-dig cyclization to form an exocyclic double bond, which eventually isomerises to the aromatic tetrahydrobenzo [g]quinoline. The mode of cyclization is discussed and supported by DFT calculations.…”