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Title

The Silylalkyne-Prins Cyclization:  Stereoselective Synthesis of Tetra- and Pentasubstituted Halodihydropyrans

AuthorsMiranda, Pedro O. ; Ramírez, Miguel A.; Martín, Víctor S.; Padrón, Juan I.
KeywordsTheoretical calculations
Alcohols
Rearrangement
Aldehydes
Cyclization
Issue Date25-Mar-2006
PublisherAmerican Chemical Society
CitationOrganic Letters 8(8): 1633–1636 (2006)
AbstractA new type of Prins cyclization using silylated secondary homopropargylic alcohols and aldehydes yielding tetra- and pentasubstituted dihydropyrans is described. The presence of the trimethylsilyl group in the triple bond favors the Prins cyclization and minimizes the 2-oxonia-[3,3]-sigmatropic rearrangement as a competitive alternative pathway. Ab initio theoretical calculations of the species involved in the rearrangements support the proposed mechanism. The process is highly stereoselective, affording cis-dihydropyran as the only isomer.
Publisher version (URL)https://doi.org/10.1021/ol060247m
URIhttp://hdl.handle.net/10261/212270
DOI10.1021/ol060247m
ISSN1523-7060
E-ISSN1523-7052
Appears in Collections:(IPNA) Artículos
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