1999
DOI: 10.1002/(sici)1099-0682(199907)1999:7<1057::aid-ejic1057>3.3.co;2-0
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Cycloisomerization of Alkynols at Transition Metal Templates

Abstract: The metal-assisted cycloisomerization of ω-alkynols to oxaand -hexynols to give the corresponding oxacycloalkylidene complexes. In some cases kinetic hydroxyalkylvinylidene cycloalkylidene complexes is reviewed. A variety of low-valent coordinatively unsaturated transition metal templates from complex intermediates can be isolated and characterized. group 6 to 10 mediate the cyclization of ω-butynols, -pentynols,

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Cited by 22 publications
(30 citation statements)
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“…[36] The first report of such a transformation dates back almost 15 years (Scheme 21). [37] Although the yields were modest, chromium, tungsten, and molybdenum carbonyl complexes were found to promote the stoichiometric cyclization of homopropargyl alcohol 64 to the corresponding Fischer carbene complexes.…”
Section: Intramolecularmentioning
confidence: 99%
“…[36] The first report of such a transformation dates back almost 15 years (Scheme 21). [37] Although the yields were modest, chromium, tungsten, and molybdenum carbonyl complexes were found to promote the stoichiometric cyclization of homopropargyl alcohol 64 to the corresponding Fischer carbene complexes.…”
Section: Intramolecularmentioning
confidence: 99%
“…The residue is purified by flash chromatography on silica to give 16 (0.21 g, 78%). Ϫ LRMS (EI ); m/z: 243 (M ϩ Ϫ 1, 2%), 137 (100), 91 (20). [74] Obtained from dihydrofuran oxide 10c (0.32 g, 1.7 mmol).…”
Section: -Benzyloxy-1-oxaspiro[45]dec-3-ene (16)mentioning
confidence: 99%
“…The cyclization of acetylenic alcohols at a metal template yields 2,3-dihydrofurans or 2,3-dihydropyrans, either directly [19] or via a carbene complex intermediate, which is subsequently cleaved by action of a base. [20] Alternatively, ring-closing metathesis of appropriately substituted enol ethers gives cyclic enol ethers related to glycals; however, use of the conveniently accessible GrubbsЈ catalyst is rather limited in these cases. [21Ϫ23] In the course of our studies directed towards the cleavage of conformationally rigid dihydropyran oxides by nucleophiles, [24] we investigated the base-promoted rearrangement of these substrates with a view towards the synthesis of 2,3-dihydropyrans and -furans.…”
Section: Introductionmentioning
confidence: 99%
“…As previously commented, alkynol derivatives can be converted into Fischer-type carbene complexes under appropriate conditions (see Scheme 1, pathway a). 5 The excellent work developed by F. E. McDonald in this field should be remarked upon at this point. 6 Thus, we considered that alkynol derivatives, such as 7, should react in the presence of group 6 derived complexes M(CO) 5 ·L (M = Cr, Mo, W; L = labile ligand) to give Fischer carbene complexes 4 via π-complexes 8 (Scheme 3).…”
Section: Introductionmentioning
confidence: 94%
“…For this purpose, we needed to work with a catalyst derived from a group 6 metallic pentacarbonyl species. However, it should be noted that group 6 metallic pentacarbonyl species M(CO) 5 are unstable and need to be stabilized by an additional ligand to form the hexacoordinated species M(CO) 5 ·L, where ligand L is usually an amine (e.g., Et 3 N) or an ether (e.g., THF). It is also important to note that these M(CO) 5 ·L species are usually generated by the irradiation (350 nm) of a solution of the corresponding hexacarbonylmetal [M(CO) 6 ] in the presence of the ligand.…”
Section: Synthesis Of Eight-membered Rings By a Pentacarbonyltungstenmentioning
confidence: 99%