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Title: | Stereoselective Intramolecular Nicholas Reaction Using Epoxides as Nucleophiles |
Authors: | Pinacho Crisóstomo, Fernando R. ![]() ![]() |
Keywords: | Ethers Protective groups Alcohols Cyclization Substitution reactions |
Issue Date: | 16-Jan-2004 |
Publisher: | American Chemical Society |
Citation: | Organic Letters 6(4): 565-568 (2004) |
Abstract: | The 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 |
URI: | http://hdl.handle.net/10261/211744 |
DOI: | 10.1021/ol0363570 |
ISSN: | 1523-7060 |
E-ISSN: | 1523-7052 |
Appears in Collections: | (IPNA) Artículos |
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accesoRestringido.pdf | Artículo principal | 16,34 kB | Adobe PDF | ![]() View/Open |
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