Nickel(0)-catalyzed diastereoselective three-component coupling of 1,3-dienes, aldehydes, and organometallic reagents: influence of organometallic reagents on diastereoselectivity

作者：Saito Nozomi; Yamazaki Tetsuro; Sato Yoshihiro^*

来源：Tetrahedron Letters, 2008, 49(34): 5073-5076.

DOI：10.1016/j.tetlet.2008.06.033

• nickel
• 1,3-diene
• aldehyde
• organometallic reagent
• multicomponent coupling
• N-heterocyclic carbene

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 PPh3 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.

• 出版日期2008-8-18