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Synfacts 2022; 18(07): 0787
DOI: 10.1055/s-0041-1737688
Organo- and Biocatalysis

Energy-Transfer-Induced Strain-Release [2π+2σ] Cycloadditions

Contributor(s):
Benjamin List
,
Vikas Kumar Singh
Guo R, Chang Y.-C, Herter L, Salome C, Braley SE, Fessard TC, Brown MK. * Indiana University, Bloomington, USA
Strain-Release [2π + 2σ] Cycloadditions for the Synthesis of Bicyclo[2.1.1]hexanes Initiated by Energy Transfer.

J. Am. Chem. Soc. 2022;
144: 7988-7994-
DOI: 10.1021/jacs.2c02976.
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Key words

energy transfer - [2π+2σ] cycloaddition - ring opening - strain release - bicyclohexanes

Significance

Brown and co-workers present a new strategy for the synthesis of bicyclo[2.2.1]hexanes by strain-release [2π+2σ] cycloadditions. A diradical­ cyclobutene, formed in situ, reacts with electronically diverse substituted olefins to give the corresponding products in poor to good yields.


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Comment

Due to their high rigidity, bicyclic[2.2.1] compounds often show higher activity, solubility and metabolic stability than substituted benzenes, making them important building blocks in drug development. However, currently available methods for the synthesis of bicyclo[2.2.1]hexanes are limited to intramolecular reactions and typically feature a narrow scope. In the highlighted approach, the authors expand the method to intermolecular reactions with a broad scope.


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Publication History

Article published online:
15 June 2022

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