Stereoselective C-Sialoside Formation

The ability of the 4-0,5-iV-oxazolidinone group to limit glycal formation prompted Crich and coworkers to revisit the use of electrophilic sialyl donors for the formation of C-sialosides. Their effort resulted in the discovery that the /V-acetyloxazolidone-protected dibutylphosphates, on activation with TMSOTf at -78°C in the presence of 

SCHEME 5.20 Use of the Ireland-Claisen rearrangement in C-sialylation. BOM, benzy-loxymethyl LiHMDS, lithium bis(trimethylsilyl)amide TMS, trimethylsilyl. 

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