Pentacoordinate Organoaluminum Chemistry: Catalytic Efficiency of Me3Al in the Epoxide Cleavage with Alkynyllithiums was written by Ooi, Takashi;Kagoshima, Naoko;Ichikawa, Hayato;Maruoka, Keiji. And the article was included in Journal of the American Chemical Society in 1999.Synthetic Route of C6H12O2 This article mentions the following:
A new and highly effective catalytic method for epoxide alkynylations was developed that involves the chelation-controlled alkylation of heterosubstituted epoxides with Me3Al via pentacoordinate organoaluminum complexes by taking advantage of the exceedingly high affinity of aluminum to oxygen. For example, reaction of epoxy ether, (1-benzyloxy)-3-butene oxide, in toluene with PhC顚咰Li under the influence of catalytic Me3Al (1h mol%) proceeded smoothly at 0 掳C for 5 h to furnish the alkynylation product, 1-(benzyloxy)-6-phenyl-5-hexyn-3-ol, in 76% yield [3% without Me3Al catalyst; 78% with stoichiometric Me3Al under similar conditions]. This represents the first catalytic procedure for the amphiphilic alkylation of epoxides. The participation of pentacoordinate Me3Al complexes of epoxy ethers is emphasized by comparing the reactivity with the corresponding simple epoxide, 5-phenyl-1-pentene oxide, which was not susceptible to nucleophile attack of PhC顚咰Li with catalytic Me3Al under similar conditions. The pentacoordinate complex formation of Me3Al with (1-benzyloxy)-3-butene oxide is characterized by low-temperature 13C and 27Al NMR spectroscopy. This approach is also applicable to the selective alkynylation of tosyl aziridines with adjacent ether functionality, which provides a promising method for amino alc. synthesis. In the experiment, the researchers used many compounds, for example, 2-Methoxytetrahydro-2H-pyran (cas: 6581-66-4Synthetic Route of C6H12O2).
2-Methoxytetrahydro-2H-pyran (cas: 6581-66-4) belongs to tetrahydropyran derivatives. Tetrahydropyrans are also used as important solvents, as chemical intermediate and as monomer for ring-opening polymerization. The bismuth chloride-assisted cross-cyclization between homoallylic alcohols and epoxides provided various benzyl tetrahydropyran derivatives. The reaction afforded good yields of desired products and occurred under mild conditions.Synthetic Route of C6H12O2
Referemce:
Tetrahydropyran – Wikipedia,
Tetrahydropyran – an overview | ScienceDirect Topics