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

Chem Commun (Camb). 2010 Dec 28;46(48):9179-81. doi: 10.1039/c0cc03669b. Epub 2010 Oct 29.

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.

Publication types

  • Research Support, N.I.H., Extramural
  • Research Support, Non-U.S. Gov't
  • Research Support, U.S. Gov't, Non-P.H.S.

MeSH terms

  • Alkenes / chemical synthesis*
  • Alkynes / chemistry*
  • Bromine / chemistry*
  • Carboxylic Acids / chemistry*
  • Catalysis
  • Chlorine / chemistry*
  • Gold

Substances

  • Alkenes
  • Alkynes
  • Carboxylic Acids
  • Chlorine
  • Gold
  • Bromine