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Abstract
A nickel-catalyzed diastereoselective alkylative three-component coupling of 1,3-diene and aldehyde with organoboron or organosilicon reagents has been realized. The diastereoselectivity was dramatically changed depending on the class of organometallic reagents. The reaction using ArB(OH) 2 in the presence of PPh 3 afforded 1,3- syn-substituted 4-penten-1-ol derivative as a single diastereomer. On the other hand, the coupling reaction with tetraorganosilicon reagent using NHC as a ligand under similar conditions exclusively produced the corresponding 1,3- anti isomer.
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