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Syntheses of Dimethyl (1S,2R)-3-Bromocyclohexa-3,5-diene-1,2-dicarboxylate and Its Enantiomer

Blüchel, Christian; Mikusek, Jiri; Willis, Anthony; Gardiner, Michael; Banwell, Martin


The title compounds, (-)-2 and (+)-2, representing potentially valuable building blocks for chemical synthesis, have each been prepared from cyclopentanone in eight steps. The pivotal one involves a resolution, through the quinine- or quinidine-promoted methanolysis of the cyclic anhydride (±)-10, leading to chromatographically separable pairs of enantiomerically pure forms of regioisomeric methyl half esters.

CollectionsANU Research Publications
Date published: 2019-12-24
Type: Journal article
Source: The Journal of organic chemistry
DOI: 10.1021/acs.joc.9b03014
Access Rights: Open Access


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