4.8 Article

Collective Synthesis of Chiral Tetrasubstituted Cyclobutanes Enabled by Enantioconvergent Negishi Cross-Coupling of Cyclobutenones

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Publisher

WILEY-V C H VERLAG GMBH
DOI: 10.1002/anie.202218008

Keywords

Collective Synthesis; Enantioconvergent; Negishi Coupling; Strained Molecules; Tetrasubstituted Cyclobutane

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The nickel catalyzed enantioconvergent Negishi coupling of 4-iodocyclobutenones with aryl or alkenyl zinc reagents is reported, leading to enantioenriched 4-substituted cyclobutenones. A modular approach to the synthesis of 1,2,3,4-tetrasubstituted cyclobutanes is demonstrated.
Cyclobutenones provide a straightforward four-carbon ring platform for further structural elaborations in that every carbon atom of the ring could be potentially functionalized. We report here a nickel catalyzed enantioconvergent Negishi coupling of 4-iodocyclobutenones with an array of aryl or alkenyl zinc reagents to access enantioenriched 4-substituted cyclobutenones, from which a modular approach to the synthesis of 1,2,3,4-tetrasubstituted cyclobutanes was demonstrated.

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