1968
DOI: 10.1002/ange.19680801505
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Neuere Untersuchungen zur Stereochemie der Cyclopropanring‐Öffnung

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Cited by 25 publications
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“…

Racemic cyclopropyl ketones undergo enantioselective rearrangement to deliver the corresponding dihydrofurans in the presence of achiral phosphoric acid as the catalyst. Agood example of this particular reactivity profile is their ability to undergo rearrangement to form more stable five-, six-, or sevenmembered cyclic compounds, [2] with the so-called Cloke-Wilson rearrangement as ar emarkable case in which cyclopropyl ketones form dihydrofurans under thermal conditions. Computational studies and control experiments support this mechanistic pathway.

Cyclopropanes are inherently reactive compounds because of their thermodynamic tendencyt ou ndergo ring-opening driven by the release of ring strain.

…”
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confidence: 99%
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“…

Racemic cyclopropyl ketones undergo enantioselective rearrangement to deliver the corresponding dihydrofurans in the presence of achiral phosphoric acid as the catalyst. Agood example of this particular reactivity profile is their ability to undergo rearrangement to form more stable five-, six-, or sevenmembered cyclic compounds, [2] with the so-called Cloke-Wilson rearrangement as ar emarkable case in which cyclopropyl ketones form dihydrofurans under thermal conditions. Computational studies and control experiments support this mechanistic pathway.

Cyclopropanes are inherently reactive compounds because of their thermodynamic tendencyt ou ndergo ring-opening driven by the release of ring strain.

…”
mentioning
confidence: 99%
“…We proceeded next to survey the performance of afamily of chiral Brønsted acids (entries [1][2][3][4][5][6][7][8], observing that while the archetypical TRIP catalyst 3a was not able to promote the reaction (entry 1), 2,2'-bis(aryl)-substituted BINOL-based phosphoric acids (3b-e)t urned out to be active catalysts (entries [2][3][4][5]. From the acids tested, 3e was found to be the best one in terms of both yield and enantiocontrol (entry 5).…”
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