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Title

Stereoselective Intramolecular Nicholas Reaction Using Epoxides as Nucleophiles

AuthorsPinacho Crisóstomo, Fernando R. ; Martín, Tomás ; Martín, Víctor S.
KeywordsEthers
Protective groups
Alcohols
Cyclization
Substitution reactions
Issue Date16-Jan-2004
PublisherAmerican Chemical Society
CitationOrganic Letters 6(4): 565-568 (2004)
AbstractThe intramolecular nucleophilic attack of the epoxides on the exo-Co2(CO)6-propargylic cations provided cyclic ethers in good yields. The use of substrates with stereochemically defined oxiranes provided polysubstituted tetrahydropyrans and oxepanes with a high degree of stereocontrol. The cyclization is sensitive to the nature of the protecting group used at the primary alcohol, the use of tert-butyl carbonates being highly effective in terms of regioselectivity and yields.
Publisher version (URL)https://doi.org/10.1021/ol0363570
URIhttp://hdl.handle.net/10261/211744
DOI10.1021/ol0363570
ISSN1523-7060
E-ISSN1523-7052
Appears in Collections:(IPNA) Artículos
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