1996
DOI: 10.1021/jo960059h
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The η4-Dienyl Tricarbonyliron Moiety in Heterocyclic Synthesis. A Rare 1,2-Migration of the Complexation Site as a Key Step for a Novel Stereoselective Preparation of trans-2,3-Disubstituted 1,4-Dioxanes

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Cited by 22 publications
(3 citation statements)
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References 17 publications
(18 reference statements)
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“…21 As their utility in a number of applications continues to be investigated, for example, in use as photoreceptors, 22 in perfumes, 23 and as anti-tumoral 24 and anti-viral agents, 25 there remains a pressing need for additional methods for their preparation. A simple derivation of the original substrates by inclusion of an oxygen atom in the tether was envisaged to allow access to 1,4-dioxanes of varying substitution patterns.…”
Section: Resultsmentioning
confidence: 99%
“…21 As their utility in a number of applications continues to be investigated, for example, in use as photoreceptors, 22 in perfumes, 23 and as anti-tumoral 24 and anti-viral agents, 25 there remains a pressing need for additional methods for their preparation. A simple derivation of the original substrates by inclusion of an oxygen atom in the tether was envisaged to allow access to 1,4-dioxanes of varying substitution patterns.…”
Section: Resultsmentioning
confidence: 99%
“…The reaction of transoid (pentadienyl)iron cations, generated via ionization of (dienyl the intermediacy of transoid pentadienyl cations has been reported to afford dienyl-fluorides 88 in a stereoselective fashion [91]. Cyclization of dienols 87, bearing a pendant heteroatom nucleophile, under acidic conditions affords 5, 6, or 8-membered ring dienyl hetero-cycles 89 and 90…”
Section: Substitution Of (Dienol)-and (Di-enyl Actate)fe(co) 3 Complexesmentioning
confidence: 99%
“…Thus far, several efficient methods, which skip the isolation of the acyclic (pentadienyl)iron(1+) cations (in situ generation), have been developed and applied to natural product synthesis. 4 Previously, we described the regio-and stereo-selective 1,5-nucleophilic substitution of the cyanophosphate Fe(CO) 3 complexes with several heteroatomic nucleophiles, giving the 1,2-migrated products of the Fe(CO) 3 group with (E,Z)configuration. 5 Here, we wish to describe the regio-and stereoselective synthesis of (E,E)-1,5-substituted adducts and their novel application to construction of contiguous stereogenic centers in acyclic alkenes (Scheme 1).…”
mentioning
confidence: 99%