Ruthenium-catalyzed cyclizations of enynes via a ruthenacyclopentene intermediate: Development of three novel cyclizations controlled by a substituent on alkyne of enyne

Three novel ruthenium-catalyzed cyclizations of enynes were developed

Nozomi Saito

2011

Scholarcy highlights

  • Three novel ruthenium-catalyzed cyclizations of enynes were developed
  • When an enyne having an alkyl, an ester, or a formyl group on an alkyne was reacted with Cp*RuCl(cod) under ethylene gas, ethylene was inserted into the ruthenium-sp2 carbon bond of ruthenacyclopentene to afford ruthenacycloheptene, and β-hydrogen elimination followed by reductive elimination occurred to give a cyclic compound having a 1,3-diene moiety
  • When an acyl group was placed on the alkyne, the carbonyl oxygen coordinated to the ruthenium metal of ruthenacyclopentene to produce a ruthenium carbene complex, which reacted with ethylene to give a cyclic compound having a cyclopropane ring on the substituent
  • On the other hand, when the substituent on the alkyne was pent-4-enyl, insertion of an alkene part into ruthenacyclopentene followed by reductive elimination gave a tricyclic compound by a ruthenium-catalyzed cyclization of diene and an alkyne

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