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Asymmetric Intramolecular Buchner Reaction: From High Stereoselectivity to Coexistence of Norcaradiene, Cycloheptatriene, and an Intermediate Form in the Solid State

Abstract : Bicyclic compounds bearing a quaternary stereogenic center have been obtained using asymmetric intramolecular Buchner reaction with excellent yields and level of enantioselectivity. X-ray crystallography determination of the absolute configuration of one product has led to the serendipitous observation of an unusual behavior within the crystal structure, with equilibrating norcaradiene and cycloheptatriene valence isomers at the solid state, as well as an even more unexpected intermediate form. DFT calculations were performed to support these observations.
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https://hal.archives-ouvertes.fr/hal-03371078
Contributor : Benjamin Darses Connect in order to contact the contributor
Submitted on : Friday, October 8, 2021 - 1:11:07 PM
Last modification on : Monday, October 11, 2021 - 11:54:52 AM

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Benjamin Darses, Pascale Maldivi, Christian Philouze, Philippe Dauban, Jean-François Poisson. Asymmetric Intramolecular Buchner Reaction: From High Stereoselectivity to Coexistence of Norcaradiene, Cycloheptatriene, and an Intermediate Form in the Solid State. Organic Letters, American Chemical Society, 2021, 23 (2), pp.300-304. ⟨10.1021/acs.orglett.0c03774⟩. ⟨hal-03371078⟩

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