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Synthetic equivalents based on Weinreb amide functionality for convenient access to monoprotected α-diketones
Date Issued
03-04-2007
Author(s)
Balasubramaniam, Sivaraman
Indian Institute of Technology, Madras
Abstract
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.