2001
DOI: 10.1021/ol0163169
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Silicon-Assisted Ring Opening of Donor−Acceptor Substituted Cyclopropanes. An Expedient Entry to Substituted Dihydrofurans

Abstract: [reaction: see text]. (tert-butyldiphenylsilyl)methylcyclopropanes undergo ring opening to furnish substituted dihydrofurans in good to excellent yields on treatment with TiCl4 in dichoromethane. The silicon that assists the regioselective ring opening is retained in the product to allow further functional group manipulations.

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Cited by 101 publications
(38 citation statements)
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“…[22] 2,3-Dihydrofurans play key roles as structural elements of biologically active compounds such as aflatoxin B 1 ,a nd they are considered very useful synthetic intermediates. [24] When irradiating am ixture of substrate 1 and 5% Mo(CNAr 3 NC) 3 in dry [D 6 ]benzene with ab lue LED at l = 455 nm in an evacuated sealed NMR tube,p roduct 2 is formed in 84 %yield (at room temperature). Thermally,t he conversion of 1 into 2 is very difficult to perform because very harsh conditions or activating groups are necessary.…”
Section: Ru(bpy)mentioning
confidence: 99%
See 1 more Smart Citation
“…[22] 2,3-Dihydrofurans play key roles as structural elements of biologically active compounds such as aflatoxin B 1 ,a nd they are considered very useful synthetic intermediates. [24] When irradiating am ixture of substrate 1 and 5% Mo(CNAr 3 NC) 3 in dry [D 6 ]benzene with ab lue LED at l = 455 nm in an evacuated sealed NMR tube,p roduct 2 is formed in 84 %yield (at room temperature). Thermally,t he conversion of 1 into 2 is very difficult to perform because very harsh conditions or activating groups are necessary.…”
Section: Ru(bpy)mentioning
confidence: 99%
“…Thermally,t he conversion of 1 into 2 is very difficult to perform because very harsh conditions or activating groups are necessary. [24] When irradiating am ixture of substrate 1 and 5% Mo(CNAr 3 NC) 3 in dry [D 6 ]benzene with ab lue LED at l = 455 nm in an evacuated sealed NMR tube,p roduct 2 is formed in 84 %yield (at room temperature). When attempting to perform the same reaction with the well-known Ir(ppy) 3 (ppy = 2-phenylpyridine) photosensitizer,noconversion is observed.…”
Section: +mentioning
confidence: 99%
“…Die Tr ansformation von 1 zu 2 ist thermisch nur schwer durchführbar,d as ehr harsche Reaktionsbedingungen oder aktivierende Gruppen vonnçten sind. [24] Wird eine Lçsung von Substrat 1 mit 5% Mo(CNAr 3 NC) 3 in wasserfreiem [D 6 ]Benzol mithilfe einer blauen LED-Lampe bei l exc = 455 nm in einem unter Va kuum versiegelten NMR-Rçhrchen bei Raumtemperatur bestrahlt, wird Produkt 2 in 84 %A usbeute erhalten. Unter identischen Bedingungen wird mit dem bekannten Photosensibilisator Ir(ppy) 3 (ppy = 2-Phenylpyridin) kein Umsatz erzielt.…”
Section: Angewandte Chemieunclassified
“…By analogy, the configuration of cyclopropanes 22,29,31, and 35 has also been determined and shows that the cis R 1 , R 3 geometry is always the major one (Scheme 5). mixture and recovery of triphenylphosphine after column chromatography.…”
mentioning
confidence: 99%
“…22 Hence, we checked whether the formation of dihydrofuran could arise from rearrangement of the cyclopropane during the reaction and choose to study the rearrangement of cyclopropane 25 formed in a reaction where dihydrofuran was also formed. Cyclopropane 25 was then heated in THF under reflux in the presence or absence of 1 equiv of LiBr (LiBr is present in cyclopropanation reaction as it is formed by reaction of n-BuLi with alkylphosphonium bromide).…”
mentioning
confidence: 99%