2018
DOI: 10.1021/acs.joc.8b01449
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Exploring Acetylene Chemistry: A Transition Metal-Free Route to Dienyl 6,8-Dioxabicyclo[3.2.1]octanes from Ketones and Acetylenes

Abstract: Dienyl derivatives of 6,8-dioxabicyclo[3.2.1]octanes, closely related to naturally abundant molecules, have been synthesized from 2-acetyl-3,4-dihydropyrans (readily available from ketones and acetylene in two steps), which further add to aryl(hetaryl)acetylenes in the KOBu/DMSO superbase system (105 °C, 1.5 h) to stereoselectively give the corresponding E-styryl adducts. The latter undergo ring closure (NHCl/HO, acetonitrile, reflux, 8 h) to form the 6,8-dioxabicyclo[3.2.1]octane core decorated with the (1 Z,… Show more

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Cited by 6 publications
(1 citation statement)
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“…Recently, dihydropyrans 2 were selectively transformed into 7-dienyl derivatives of 6,8-DOBCO via superbase-mediated vinylation with arylacetylenes and acid-catalyzed cyclization of the intermediate unsaturated ketones (Scheme 1B). 15…”
Section: Introductionmentioning
confidence: 99%
“…Recently, dihydropyrans 2 were selectively transformed into 7-dienyl derivatives of 6,8-DOBCO via superbase-mediated vinylation with arylacetylenes and acid-catalyzed cyclization of the intermediate unsaturated ketones (Scheme 1B). 15…”
Section: Introductionmentioning
confidence: 99%