Allylboration of Aldehydes

allylboration - aldehydes - TRIP

Significance

<P>A highly enantioselective allylboration of aldehydes catalyzed by the chiral Brønsted acid (R)-TRIP is reported by the authors. This transformation shows a broad substrate scope: aryl, heteroayrl, α,β-unsaturated and aliphatic aldehydes can all be efficiently allylated. Furthermore, the crotylboration of benzaldehyde also proceeded smoothly with high diastereo- and enantioselectivity in the presence of this acid ­catalyst.</P>

Comment

<P>Simple starting materials and a commercially available catalyst make this protocol a useful and efficient method for the synthesis of enantioenriched homoallylic alcohols. A transition state where the boronate is activated by protonation of the boronate oxygen with a chiral phosphoric acid is proposed by the authors. To confirm this activation model, further mechanistic investigation may be required.</P>