Gold(I) catalyzed isomerization of 5-en-2-yn-1-yl acetates: An efficient access to acetoxy bicyclo[3.1.0]hexenes and 2-cycloalken-1-ones

Andrea Buzas (1) , Fabien Gagosz (1)

1 DCSO - Laboratoire de synthèse organique

The gold(I) catalyzed rearrangement of 5-en-2-yn-1-yl acetates into functionalized acetoxy bicyclo[3.1.0]hexenes is described. The mild reaction conditions employed allow the efficient and rapid synthesis of a variety of such bicyclic compounds via a sequence of two gold(I)-catalyzed isomerization steps. Acetoxy bicyclo[3.1.0]hexenes products can be further transformed to 2-cycloalkenones by simple methanolysis. Copyright © 2006 American Chemical Society.

Domains: Organic chemistry

Andrea Buzas, Fabien Gagosz. Gold(I) catalyzed isomerization of 5-en-2-yn-1-yl acetates: An efficient access to acetoxy bicyclo[3.1.0]hexenes and 2-cycloalken-1-ones. Journal of the American Chemical Society, 2006, 128 (39), pp.12614-12615. ⟨10.1021/ja064223m⟩. ⟨hal-00951310⟩