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Reenvisioning the De Mayo Reaction: A Boron-Enabled Cycloaddition Approach
Neetu Sharma1, Yanyao Liu1, Partha Sarathi Hazra1
1Department of Chemistry, Indiana University, Bloomington, Indiana, USA.
Abstract:
The De Mayo reaction is an established process in chemical synthesis for the synthesis of 1,5-dicarbonyls or cyclobutanols in selected cases. Herein, we present a reevisioned approach that utilizes alkenylboronates as surrogates for 1,3-dicarbonyls. The process allows for delayed controlled synthesis of the traditional De Mayo products. Elaboration of the C─B bond in the product was also demonstrated. A key aspect of the study is the identification of a rigid oxy-boracycle as a key intermediate to allow for bimolecular cycloaddition to occur. Mechanistic experiments are provided to clarify the importance of the chelate.
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