Seven-membered-ring <i>trans</i>-alkenes undergo rapid, uncatalyzed carboboration reactions to form trialkylboranes as single diastereomers. Products formed from this reaction are air-stable, contrasting with other trialkylboranes, which can ignite in the presence of oxygen. Up to five consecutive stereocenters can be constructed around the ring in three synthetic steps with a single purification. Control experiments and computational studies support a concerted mechanism for the 1,2-carboboration, similar to the mechanism for hydroboration. Hindered trialkylboranes can undergo reverse hydroboration reactions to form allylic silanes or can be fully oxidized to afford highly substituted triols.

Uncatalyzed 1,2-carboboration of seven-membered-ring <i>trans</i>-alkenes

254th National Meeting (2017)

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Uncatalyzed 1,2-carboboration of seven-membered-ring trans-alkenes