Rh(II)-Catalyzed Spirocyclization of α‑Diazo Homophthalimides with Cyclic Ethers

Rh­(II)-catalyzed decomposition of α-diazo homophthalimides in the presence of cyclic ethers gave spirocyclic products of Stevens-type [1,2]-alkyl shift within the postulated oxonium ylide intermediate. Such a reaction pathway is in line with thermodynamic predictions obtained from quantum chemical...

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Bibliographic Details
Published in:Journal of organic chemistry 2019-04, Vol.84 (7), p.4534-4542
Main Authors: Guranova, Natalia I, Dar’in, Dmitry, Kantin, Grigory, Novikov, Alexander S, Bakulina, Olga, Krasavin, Mikhail
Format: Article
Language:English
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Summary:Rh­(II)-catalyzed decomposition of α-diazo homophthalimides in the presence of cyclic ethers gave spirocyclic products of Stevens-type [1,2]-alkyl shift within the postulated oxonium ylide intermediate. Such a reaction pathway is in line with thermodynamic predictions obtained from quantum chemical calculations performed at the B3LYP/6-31G* and B3LYP/6-311++G** levels of theory. These findings represent the first systematically investigated case of spirocyclization of cyclic α-diazocarbonyl compounds with cyclic ethers.
ISSN:0022-3263
1520-6904
DOI:10.1021/acs.joc.9b00245