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In situ generation of 2,3-allenolates in the coupling of secondary homopropargylic alcohols and aldehydes

AuthorsMiranda, Pedro O. ; Ramírez, Miguel A.; Padrón, Juan I. ; Martín, Víctor S.
Keywords[3,3]-Sigmatropic rearrangement
Prins cyclization
Iron(III) halides
Issue Date16-Jan-2006
CitationTetrahedron Letters 47(3): 283-286 (2006)
AbstractA study on a novel oxonia [3,3]-sigmatropic rearrangement as competitive alternative pathway to the acetylenic Prins cyclization on the addition of secondary homopropargylic alcohols to aldehydes catalyzed by iron(III) is described. ‘Ab initio’ theoretical calculations of the species involved on the rearrangement supports the in situ formation of 2,3-allenolates. The domino process involves three consecutive chemical events in one-pot format reaction (∼70% average).
Publisher version (URL)https://doi.org/10.1016/j.tetlet.2005.11.032
Appears in Collections:(IPNA) Artículos
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