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

✍ Scribed by Nozomi Saito; Tetsuro Yamazaki; Yoshihiro Sato

• Book ID: 104095517
• Publisher: Elsevier Science
• Year: 2008
• Tongue: French
• Weight: 211 KB
• Volume: 49
• Category: Article
• ISSN: 0040-4039
• DOI: 10.1016/j.tetlet.2008.06.033

✦ Synopsis

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.