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Alcaide, B. et al.

Benito Alcaide, Pedro Almendros, Teresa Martínez del Campo, María C. Redondo, Israel Fernández,

Striking alkenol versus allenol reactivity: metal-catalyzed chemodifferentiating oxycyclization of enallenols.

An efficient chemodivergent metal-controlled methodology for the generation of different highly functionalized oxygen heterocycles from common enallenol substrates has been developed. Chemoselectivity control in the O-C functionalization of an enallenol can be achieved through the choice of catalyst: AuCl(3), PdCl(2), and [PtCl(2)(CH(2)=CH(2))](2) exclusively afford dihydrofurans through selective activation of the allenol moiety, whereas FeCl(3) solely gives tetrahydrofurans or tetrahydropyrans through selective activation of the alkenol moiety. We have also shown that a combination of metal-mediated hydroalkoxylation and allenic aminocyclization reactions can lead to a useful preparation of the tetrahydrofuro[3,2-b]piperidine core of the antimalarial alkaloid isofebrifugine. These divergent heterocyclization reactions have been developed experimentally and additionally, their mechanisms have been investigated by a theoretical study.[1]

References

Striking alkenol versus allenol reactivity: metal-catalyzed chemodifferentiating oxycyclization of enallenols. Alcaide, B., Almendros, P., Martínez del Campo, T., Redondo, M.C., Fernández, I. Chemistry (2011) [Pubmed]

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