Palladium-Catalyzed Allylation of Aryl Halides with Homoallyl Alcohols Bearing a Trisubstituted Double Bond: Application to Chirality Transfer from Hydroxylated Carbon to Benzylic One
作者:Ryota Wakabayashi、Daishi Fujino、Sayuri Hayashi、Hideki Yorimitsu、Koichiro Oshima
DOI:10.1021/jo100857d
日期:2010.7.2
A facile route to homoallyl alcohols bearing a trisubstituted double bond has been devised. The palladium-catalyzed reactions of aryl halides with the alcohols thus synthesized result in regiospecific allyl transfer from the alcohols to aryl halides via retro-allylation, providing allylarenes having two substituents at the 1 and 2 positions of the allyl moiety. Optically active homoallyl alcohols transfer
已经设计了一种容易的途径来制备带有三取代的双键的均烯丙基醇。钯催化的芳基卤化物与如此合成的醇的反应导致区域特异性的烯丙基经由逆向烯丙基化从醇向芳基卤化物的转移,提供了在烯丙基部分的1和2位具有两个取代基的烯丙基芳烃。旋光性均烯丙基醇将其在羟基化碳上的手性转移至产物的苄基碳。