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. 2015 Jun 5;17(11):2824-7.
doi: 10.1021/acs.orglett.5b01244. Epub 2015 May 21.

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

Yoshikazu Horino  1 , Ataru Aimono  1 , Hitoshi Abe  1
Affiliations

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

Yoshikazu Horino et al. Org Lett. .

Abstract

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.

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