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

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Asymmetric Intramolecular Buchner Reaction: From High Stereoselectivity to Coexistence of Norcaradiene, Cycloheptatriene, and an Intermediate Form in the Solid State
Organic Letters ( IF 4.9 ) Pub Date : 2021-01-04 , DOI: 10.1021/acs.orglett.0c03774
Benjamin Darses _{1,

2} , Pascale Maldivi ₃ , Christian Philouze ₁ , Philippe Dauban ₂ , Jean-François Poisson ₁

Affiliation

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.

中文翻译：

不对称分子内布氏反应：从高立体选择性到降丁卡丹，环庚三烯和固态中间体的共存

使用不对称分子内布氏反应以优异的收率和对映选择性水平获得了带有季立体中心的双环化合物。X射线晶体学测定一种产物的绝对构型已导致偶然观察到晶体结构内的异常行为，使降冰片烯和环庚三烯化合价异构体处于固态平衡，甚至是出乎意料的中间形式。进行DFT计算以支持这些观察。

更新日期：2021-01-16

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