sitagliptin-phosphate and allyl-bromide

Sarcosine was discovered to be an excellent ligand for cobalt-catalyzed carbon-carbon cross-coupling of Grignard reagents with allylic and vinylic bromides. The Co(II)/sarcosine catalytic system is shown to perform efficiently when phenyl and benzyl Grignards are coupled with alkenyl bromides. Notably, previously unachievable Co-catalyzed coupling of allylic bromides with Grignards to linearly coupled α-products was also realized with Co(II)/sarcosine catalyst. This method was used for efficient preparation of the key intermediate in an alternative synthesis of the antihyperglycemic drug sitagliptin.

Topics: Allyl Compounds; Catalysis; Cobalt; Hypoglycemic Agents; Indicators and Reagents; Ligands; Molecular Structure; Sarcosine; Sitagliptin Phosphate; Vinyl Compounds