Synthesis and Reactions of 1-Alkenyl-1,1-Heterobimetallic Reagents

Significance

While several routes have been described for the generation of 1-alkenyl-1,1-heterobimetallic species bearing a boron moiety, this new approach, based on relatively stable 1-alkynyl pinacolborates, is now the most convenient for synthetic purposes. The generated zinc-boron species were shown to attack chiral aldehydes with high diastereoselectivity, giving a useful route to chiral allylic alcohols and their multiple derivatives. The described synthetic sequences are conducted in one pot with excellent overall yields.