We recently reported the stereoselective copper-catalyzed cross-coupling reaction of cyclic allylboronic acids and α-diazoketones. The relative configuration of the product is retained, indicating syn stereochemistry for the replacement of the B(OH)2 group. Competitive cross-coupling of trans and cis cyclic allylboronic acids with α-diazoketones indicates different reactivity for the two diastereoisomers. Based on our results, we propose that the cross-coupling reaction proceeds via a syn SE2’-type transmetalation of the allylboronic acid with a Cu-carbene species.

Mechanistic investigations of the copper-catalyzed stereoselective cross-coupling of cyclic allylboronic acids with α-diazoketones

255th National Meeting (2018)

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