Beilstein J. Org. Chem.2014,10, 1462–1470, doi:10.3762/bjoc.10.150
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Keywords: aza-prostaglandinanalogue; 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-prostaglandinanalogue [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-prostaglandinanalogue.
Optimisation
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Graphical Abstract
Figure 1:
Bioactive molecules I [19], II [26], III & IV [21,22] with 3(2H)-furanone moiety.