Synthetic equivalents based on Weinreb amide functionality for convenient access to monoprotected α-diketones

A convenient new strategy for the synthesis of monoprotected α-diketones has been achieved. The strategy is based on the use of hitherto unreported N-methoxy-N-methyl-1,3-dithiolane-2-carboxamide and N-methoxy-N-methyl-1,3-dithiane-2-carboxamide as synthetic equivalent for an α-dicarbonyl unit with opposing polarity. Nucleophilic addition on the amide functionality followed by alkylation furnished the targeted monoprotected α-diketones in moderate to good yields. © Georg Thieme Verlag Stuttgart.