Synthesis of Chiral 3-Substituted Phthalides via Rhodium(I)-catalyzed Crossed Alkyne Cyclotrimerisation

Abstract
3-Substituted phthalides were synthesized for the first time by crossed alkyne cyclotrimerisations with Wilkinson’s catalyst. Esterification of propiolic acids with chiral propargylic alcohols by either the DCC/DMAP or the Mitsunobu method allows the synthesis of either enantiomeric form of diyne esters, that are used in crossed alkyne cyclotrimerisations with acetylene to provide 3-substituted phthalides in both enantiomeric forms.

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