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Pd-Catalyzed Three-Component Reaction of 3‑(Pinacolatoboryl)ally Acetates, Aldehydes, and Organoboranes: A New Entry to Stereoselective Synthesis of (Z)-anti-Homoallylic Alcohols

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journal contribution
posted on 05.06.2015, 00:00 by Yoshikazu Horino, Ataru Aimono, Hitoshi Abe
The Pd-catalyzed three-component reaction of 3-(pinacolato­boryl)­allyl acetates, aldehydes, and organoboranes is described. The reaction is initiated by the formation of an allylic gem-palladium/boryl intermediate, which then undergoes allylation of aldehydes by allylboronates followed by a coupling reaction of in situ generated (Z)-vinylpalladium acetates with organoboranes to provide the (Z)-anti-homoallylic alcohols with high levels of diastereoselectivity and alkene stereocontrol.