The dimethylsulfoxonium methylide was treated with esters under mild conditions to rapidly afford the corresponding carboxylic acids at room temperature. Moreover, by performingthe procedure on enantiopure substrates, it wasdemonstrated that the reaction occurs without racemization.18O-labeled reagents showed that the reaction does not proceed through an ester hydrolysis mechanism. The reactions are characterized by an unusual reactivity of the dimethylsulfoxonium methylide. This methodology is general and can beconsidered a valid alternate route for ester cleavage when a substrate is sensitive to hydrolysis conditions.
Unusual Reactivity of Dimethylsulfoxonium Methylide with Esters
Antonella Leggio
;
2012-01-01
Abstract
The dimethylsulfoxonium methylide was treated with esters under mild conditions to rapidly afford the corresponding carboxylic acids at room temperature. Moreover, by performingthe procedure on enantiopure substrates, it wasdemonstrated that the reaction occurs without racemization.18O-labeled reagents showed that the reaction does not proceed through an ester hydrolysis mechanism. The reactions are characterized by an unusual reactivity of the dimethylsulfoxonium methylide. This methodology is general and can beconsidered a valid alternate route for ester cleavage when a substrate is sensitive to hydrolysis conditions.File in questo prodotto:
Non ci sono file associati a questo prodotto.
I documenti in IRIS sono protetti da copyright e tutti i diritti sono riservati, salvo diversa indicazione.
