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Title

Direct Access to 2,3,4,6-Tetrasubstituted Tetrahydro-2H-pyrans via Tandem SN2′–Prins Cyclization

AuthorsScoccia, Jimena; Pérez, Sixto J.; Sinka, Victoria; Cruz, Daniel A.; López-Soria, Juan M.; Fernández, Israel; Martín, Víctor S.; Miranda, Pedro O. CSIC ORCID ; Padrón, Juan I. CSIC ORCID
Issue Date31-Aug-2017
PublisherAmerican Chemical Society
CitationOrganic Letters 19(18): 4834-4837 (2017)
AbstractA new, direct, and diastereoselective synthesis of activated 2,3,4,6-tetrasubstituted tetrahydro-2H-pyrans is described. In this reaction, iron(III) catalyzed an SN2′–Prins cyclization tandem process leading to the creation of three new stereocenters in one single step. These activated tetrahydro-2H-pyran units are easily derivatizable through CuAAC conjugations in order to generate multifunctionalized complex molecules. DFT calculations support the in situ SN2′ reaction as a preliminary step in the Prins cyclization.
Publisher version (URL)https://doi.org/10.1021/acs.orglett.7b02270
URIhttp://hdl.handle.net/10261/184912
DOI10.1021/acs.orglett.7b02270
ISSN1523-7060
E-ISSN1523-7052
Appears in Collections:(IPNA) Artículos

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