Diels-Alder Cycloadditions of Oxacyclic Allenes and α-Pyrones
Laura G Wonilowicz1, Milauni M Mehta1, Lisa L Kamecke1
1Department of Chemistry and Biochemistry, University of California, Los Angeles, California 90095-1569, United States.
Abstract:
Reactions of α-pyrones with oxacyclic allenes in Diels-Alder trappings are described. We investigate regioselectivity trends and perform competition experiments to assess the influence of structural and electronic features on relative reaction rates. We also demonstrate the stereospecific trapping of an oxacyclic allene, which proceeds in high optical yield. This study provides insight into strained cyclic allene reactivity, as well as new synthetic tools for the rapid construction of complex, heterocyclic scaffolds.
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