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The reactivity of boronate complexes which resemble donor–acceptor cyclopropanes is described. The enantioenriched cyclopropyl boronate complexes were shown to undergo concerted 1,2-metalate rearrangement/ring opening upon activation with a Lewis acid. This method provides atom-efficient access to optically active γ-carbonyl boronic esters in moderate to excellent yields with complete enantiospecificity. Furthermore, a three-component variant of the reaction was established through in situ alkylation, and the synthetic utility of the products as chiral building blocks was demonstrated.
Gregson, C. H. U., Ganesh, V., & Aggarwal, V. K. (2019). Strain Release of Donor–Acceptor Cyclopropyl Boronate Complexes. Organic Letters, 21(9), 3412-3416. https://doi.org/10.1021/acs.orglett.9b01152