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

Christian G. Blüchel; Jiri Mikusek; Anthony C. Willis; Michael G. Gardiner; Martin G. Banwell

doi:10.1021/acs.joc.9b03014

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

Christian G. Blüchel, Jiri Mikusek, Anthony C. Willis, Michael G. Gardiner, Martin G. Banwell^*

^*Corresponding author for this work

Research output: Contribution to journal › Article › peer-review

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Abstract

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.

Original language	English
Pages (from-to)	2303-2311
Number of pages	9
Journal	Journal of Organic Chemistry
Volume	85
Issue number	4
DOIs	https://doi.org/10.1021/acs.joc.9b03014
Publication status	Published - 21 Feb 2020

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abstract = "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.",

author = "Bl{\"u}chel, {Christian G.} and Jiri Mikusek and Willis, {Anthony C.} and Gardiner, {Michael G.} and Banwell, {Martin G.}",

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AU - Willis, Anthony C.

AU - Gardiner, Michael G.

AU - Banwell, Martin G.

PY - 2020/2/21

Y1 - 2020/2/21

N2 - 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.

AB - 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.

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

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