Diastereoselective synthesis of (Z)- and (E)-homoallylic alcohols using a Pd-catalyzed three-component reaction of 3-(pinacolatoboryl)allyl benzoates, aldehydes, and aryl stannanes was developed, which provides an alternative method for the allylboration of aldehydes using α,γ-diaryl-substituted allylboronates. Both sets of reaction conditions enable access to either (Z)- or (E)-homoallylic alcohols with good to high alkene stereocontrol. The present method showed good functional group compatibility and generality. Efficient chirality transfer reactions to afford enantioenriched (Z)- and (E)-homoallylic alcohols were also achieved.

The reaction tolerates 1‐aryl as well as 1‐hetaryl substituted 3‐(tri‐n‐butylstannyl)allyl acetates, aryl, hetaryl, alkenyl as well as alkyl aldehydes and various boranes.

No abstract

A synthesis of (Z)-alkene-containing linear conjugated dienyl homoallylic alcohols by using a palladium-catalyzed three-component reaction has been developed. This method shows good functional-group compatibility and generality, with high diastereoselectivity. Additionally, in many cases, the present method controls the alkene stereochemistry of the newly formed C–C bond and overcomes the inherent preference for (E)-alkene formation, giving (Z,E)- and (Z,Z)-products.

The reaction tolerates 1‐aryl as well as 1‐hetaryl substituted 3‐(tri‐n‐butylstannyl)allyl acetates, aryl, hetaryl, alkenyl as well as alkyl aldehydes and various boranes.