The use of Br/Cl to promote regioselective gold-catalyzed rearrangement of propargylic carboxylates: an efficient synthesis of (1Z, 3E)-l-bromo/chloro-2-carboxy-l,3-dienes

摘要

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