Cyclopropanation of vinyl boronates and subsequent derivatization of the boronate handle is a convenient strategy to quickly build molecular complexity. Herein, the asymmetric cyclopropanation of enantioenriched hydrobenzoin-derived vinyl boronic esters towards the synthesis of tertiary and secondary cyclopropyl boronates is disclosed. Synergistic effects between the chiral diol moiety and the amide ligand are crucial to achieving high yields and diastereoselectivities for a wide array of substrates. Mechanistic experiments unveil an unexpected lack of influence of the chiral environment of the ligand.

Asymmetric synthesis of tertiary and secondary cyclopropyl boronates via cyclopropanation of enantioenriched vinyl boronic esters

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