Organotransition metal modified sugars. Part 23. Synthesis of vinylcarbene chromium complexes containing a C-monosaccharide ligand

Abstract Organometallic C -glycosides containing a chromium carbene functionality have been synthesized from pentacarbonyl[(methoxy)methylcarbene]chromium ( 1 ) in a TiCl 4 -assisted aldol condensation with formyl glycosides. The condensation is trans -selective to give a 54–82% yield of chromium vinylcarbene C -glycosides 5 , 6 and 8 which are promising candidates for subsequent Diels–Alder, Michael addition, benzannulation and cyclopropanation reactions.