SmI(2)/Pd(0)-Mediated Intramolecular Coupling between Propargylic Esters and Tethered Aldehydes or Ketones.

A SmI(2)/Pd(0)-promoted intramolecular coupling between propargylic esters and carbonyl compounds is described. The reaction affords homopropargyl cycloalkanol products. Cyclopentanols are formed in high yields when ketones are employed as the carbonyl components, but aldehydes are found not to be suitable partners in these reactions.