Reenvisioning the De Mayo Reaction: A Boron‐Enabled Cycloaddition Approach
Abstract
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.
Article Details
Authors (6)
Neetu Sharma
Yanyao Liu
Department of Chemistry, Indiana University, 800 East Kirkwood Avenue, Bloomington, Indiana 47405, United States
Partha Sarathi Hazra
Department of Chemistry Indiana University Bloomington Indiana USA
Evan B. Piper
Department of Chemistry, Indiana University, 800 East Kirkwood Avenue, Bloomington, Indiana 47405, United States
Ryan Van Hoveln
Department of Chemistry and Physics, Indiana State University, 600 Chestnut Street, Terre Haute, Indiana 47809, United States
Michael Kevin Brown
Department of Chemistry Indiana University Bloomington Indiana USA