Ruthenium(0) catalysts promote hydrohydroxyalkylation of vicinal diols and a-hydroxy carbonyl compounds with acrylates to afford spirocyclic lactones in good to excellent yield. The redox-independent nature of the reaction is illustrated by the coupling of methyl acrylate with hydrobenzoin, benzoin, or benzil to give the same product. N-benzyl-3-hydroxyoxindole couples with an assortment of acrylic esters to give indole-containing cycloadducts. Under the conditions of ruthenium(0) catalyzed hydrohydroxyalkylation, hydroxyl-substituted methacrylate and diols form a-exo-?-butryolactones.

Ruthenium catalyzed hydrohydroxyalkylation of acrylates with diols and a-hydroxycarbonyl compounds to form spiro- and a-methylene-?-butyrolactones

247th National Meeting (2014)

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