The Use of Br/Cl to Promote Regioselective Gold-Catalyzed Rearrangement of Propargylic Carboxylates: An Efficient Synthesis of (1Z 3E)-1-Bromo/Chloro-2-Carboxy-13-Dienes

摘要

A gold-catalyzed synthesis of 1-bromo/chloro-2-carboxy-1,3-dienes is developed using propargylic carboxylates containing halogenated alkynes as substrates. The reaction is highly diastereoselective, and the halogen atom at the alkyne terminus promotes selectively 1,2-acyloxy migration. The diene products participate in the Diels-Alder and cross-coupling reactions.