Gold-Catalyzed Regioselective Meyer-Schuster Rearrangement and Ring Expansion Cascade Leading to alpha-Hydroxy-alpha-vinylcyclopentanones

Abstract

Readily available cyclobutanols having a butyne-1,4-diol moiety underwent a sequential regioselective Meyer-Schuster rearrangement and 1,2-shift, furnishing alpha-hydroxy-alpha-vinylcyclopentanones. The reaction mechanism is consistent with the formation of an allenol intermediate that racemizes under the reaction conditions. Subsequent activation of the allenol leads to an enantio- and diastereoselective route to this scaffold.