DABO Boronate Promoted Conjugate Allylation of α,ß-Unsaturated Aldehydes Using Copper(II) Catalysis.

ABSTRACT

The first catalytic method for the selective 1,4-conjugate allylation of α,ß-unsaturated aldehydes is reported. The method employs an air-stable diethanolamine-complexed boronic acid (DABO boronate) as the allyl transfer reagent and promotes conjugate addition over 1,2-addition. A variety of aryl- and alkyl-substituted enals are tolerated, providing δ,ε-unsaturated aldehyde products in good yields and selectivities under mild conditions.