Iron(III)-Catalyzed Prins-Type Cyclization Using Homopropargylic Alcohol: A Method for the Synthesis of 2-Alkyl-4-halo-5,6-dihydro-2H-pyrans
A 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.
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| Main Authors: | , , , , |
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| Other Authors: | |
| Format: | artículo biblioteca |
| Language: | English |
| Published: |
American Chemical Society
2003-05-07
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| Subjects: | Alcohols, Aldehydes, Inorganic compounds, Cyclization, Halogens, |
| Online Access: | http://hdl.handle.net/10261/212296 http://dx.doi.org/10.13039/501100006280 |
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