A new Co(0) complex mediated synthesis of C-glycoside analogues

✍ Scribed by Fulvia Orsini; Emanuela Di Teodoro

• Book ID: 104360005
• Publisher: Elsevier Science
• Year: 2003
• Tongue: English
• Weight: 436 KB
• Volume: 14
• Category: Article
• ISSN: 0957-4166
• DOI: 10.1016/s0957-4166(03)00533-0

✦ Synopsis

Properly protected glyconolactones, readily available from the parent sugars, react under mild conditions with a-bromoacetates in the presence of a soluble Co(0) complex, either in stoichiometric or substoichiometric amounts, to give a Reformatsky-type addition product to the lactone. The addition product can be subsequently converted into a variety of compounds: dehydroxylation with triethylsilane in the presence of boron trifluoride affords C-glycosides.