A tandem Mannich addition–palladium catalyzed ring-closing route toward 4-substituted-3(2H)-furanones

• Jubi John,
• Eliza Târcoveanu,
• Peter G. Jones and
• Henning Hopf

Beilstein J. Org. Chem. 2014, 10, 1462–1470, doi:10.3762/bjoc.10.150

• . Keywords: aza-prostaglandin analogue; 3(2H)-furanone; Mannich addition; palladium catalysis; tandem reaction; Introduction Organic chemists welcome the introduction of facile tandem protocols because of the advantages of multiple bond formation in one-pot processes, which in turn makes the process

• aza-prostaglandin analogue [26] 27 was isolated in 85% yield (Scheme 5). Conclusion We have developed an efficient protocol for the synthesis of 4-substituted 3(2H)-furanones by the reaction of imines or diazo esters with 4-chloroacetoacetates under palladium catalysis. We could extend the reaction to

• synthesis of 3(2H)-furanones from activated alkenes [40]. Pd-catalyzed synthesis of 3(2H)-furanone from tosylimine 1a. Mechanism of formation of the 3(2H)-furanone derivative from an imine. Pd-catalyzed synthesis of 3(2H)-furanone from diazoester 19a. Synthesis of aza-prostaglandin analogue. Optimisation