The palladium-catalysed arylation/vinylation of alpha -methylene-gamma -butyrolactone (1) proceeds in good yield, mainly to give stereodefined aryl/vinyl-substituted alpha -alkylidene-gamma -butyrolactones 4. In addition, the palladium-catalysed arylation of alpha -methylene-gamma -butyrolactone (1) may be directed towards the synthesis of 3-benzylfuran-2(5H)-ones 3 when the starting aryl iodides contain groups with electron-withdrawing conjugative properties. The combined palladium-catalysed coupling/hydrogenation reactions represent a new, simple route to functionalised 3-alkyl-gamma -butyrolactones 5, giving prominence to the possibility of stereocontrol in the formation of the new stereocentres
Palladium-Catalysed Vinilic substitution of aryl/vinyl iodides and triflates with a-methylene-g-butyrolactone-an application to the synthesis of 3-alkyl-g-butyrolactones through combined palladium-catalysed coupling/hydrogenation reaction
ARCADI, Antonio;MARINELLI, Fabio
2001-01-01
Abstract
The palladium-catalysed arylation/vinylation of alpha -methylene-gamma -butyrolactone (1) proceeds in good yield, mainly to give stereodefined aryl/vinyl-substituted alpha -alkylidene-gamma -butyrolactones 4. In addition, the palladium-catalysed arylation of alpha -methylene-gamma -butyrolactone (1) may be directed towards the synthesis of 3-benzylfuran-2(5H)-ones 3 when the starting aryl iodides contain groups with electron-withdrawing conjugative properties. The combined palladium-catalysed coupling/hydrogenation reactions represent a new, simple route to functionalised 3-alkyl-gamma -butyrolactones 5, giving prominence to the possibility of stereocontrol in the formation of the new stereocentresPubblicazioni consigliate
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