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-1,3-dienes

Yanzhao Wang, Biao Lu, Liming Zhang

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Abstract

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 selectively promotes a 1,2-acyloxy migration. The diene products participate in the Diels-Alder and cross-coupling reactions.

Original languageEnglish (US)
Pages (from-to)9179-9181
Number of pages3
JournalChemical Communications
Volume46
Issue number48
DOIs
StatePublished - Dec 28 2010

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