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Title

Iron(III)-Catalyzed Prins-Type Cyclization Using Homopropargylic Alcohol:  A Method for the Synthesis of 2-Alkyl-4-halo-5,6-dihydro-2H-pyrans

AuthorsMiranda, Pedro O. ; Díaz Díaz, David ; Padrón, Juan I. ; Bermejo, Jaime ; Martín, Víctor S.
KeywordsAlcohols
Aldehydes
Inorganic compounds
Cyclization
Halogens
Issue Date7-May-2003
PublisherAmerican Chemical Society
CitationOrganic Letters 5(11): 1979–1982 (2003)
AbstractA new Prins-type cyclization between homopropargylic alcohol and aldehydes in the presence of FeX3 to obtain 2-alkyl-4-halo-5,6-dihydro-2H-pyrans in good yield is described. Osmium-catalyzed cis dihydroxylation provided direct access to trans-2-alkyl-3-hydroxy-tetrahydro-pyran-4-ones. Anhydrous ferric halides are also shown to be excellent catalysts for the standard Prins cyclization using homoallylic alcohol. Isolation of an intermediate acetal provides substantiation of a proposed mechanism.
Publisher version (URL)https://doi.org/10.1021/ol034568z
URIhttp://hdl.handle.net/10261/212296
DOI10.1021/ol034568z
ISSN1523-7060
E-ISSN1523-7052
Appears in Collections:(IPNA) Artículos
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