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Keywords:

  • asymmetric catalysis;
  • enantioselectivity;
  • hydrogen transfer;
  • iridium;
  • propargylation
Thumbnail image of graphical abstract

It takes alkynes! Exposure of propargyl chlorides to primary benzylic alcohols in the presence of [Ir(cod){(R)-segphos}]OTf (cod=1,5-cyclooctadiene, segphos=5,5′-bis(diphenylphosphino)-4,4′-bi-1,3-benzodioxole, Tf=trifluoromethanesulfonyl) results in hydrogen exchange to give allenyliridium–aldehyde pairs that combine to form products of propargylation with high ee value (see scheme). The reaction can also be conducted using aldehydes.