Neetu Sharma, Liu Y, Partha Sarathi Hazra, Evan B. Piper, Ryan Van Hoveln, Michael Kevin Brown
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.