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Enantioselective Desymmetrization of Cyclobutanones: A Speedway to Molecular Complexity

Cyclobutanones hold a privileged role in enantioselective desymmetrization because their inherent ring strain allows for a variety of unusual reactions to occur. Current strategies include α‐functionalization, rearrangement, and C−C bond activation to directly convert cyclobutanones into a wide rang...

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Bibliographic Details
Published in:Angewandte Chemie International Edition 2020-04, Vol.59 (18), p.6964-6974
Main Authors: Sietmann, Jan, Wiest, Johannes M.
Format: Article
Language:English
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Summary:Cyclobutanones hold a privileged role in enantioselective desymmetrization because their inherent ring strain allows for a variety of unusual reactions to occur. Current strategies include α‐functionalization, rearrangement, and C−C bond activation to directly convert cyclobutanones into a wide range of enantiomerically enriched compounds, including many biologically significant scaffolds. This Minireview provides an overview of state‐of‐the‐art methods that generate complexity from prochiral cyclobutanones in a single operation. Take the strain: The ring strain of cyclobutanones makes them ideal for enantioselective desymmetrization. α‐Functionalization, rearrangement, and C−C bond activation can be used to directly convert cyclobutanones into enantiomerically enriched compounds, including many biologically significant scaffolds. This Minireview provides an overview of state‐of‐the‐art methods that generate complexity from prochiral cyclobutanones in a single operation.
ISSN:1433-7851
1521-3773
DOI:10.1002/anie.201910767