Indium-mediated coupling reactions of δ-oxygenated allyl halide derivatives 1 with aldehydes in aqueous media proceeded at the γ-position to give diol derivatives 2. Compound 1 is equivalent to an allylic carbanion 4 with a neighboring oxygen functional group generated in aqueous media.
Synthesis of Pinacol Allylic Boronic Esters via Olefin Cross-Metathesis between Pinacol Allylboronate and Terminal or Internal Alkenes
作者:Yasunori Yamamoto、Miki Takahashi、Norio Miyaura
DOI:10.1055/s-2002-19356
日期:——
The ruthenium-catalyzed olefin cross-metathesis between pinacol allylboronate, CH2=CHCH2B(O2C2Me4), and RCH=CH2 giving RCH=CHCH2B(O2C2Me4) was carried out in refluxing CH2Cl2 in the presence of an alkylidene-ruthenium complex (3 mol%).
Allyliccarbonates were more active than the corresponding allylic acetates in carbonylallylationusingPdCl2(PhCN)2-SnCl2, and the carbonylallylation by (E)-crotyl carbonate at 10 °C exhibited opposite diastereo-selectivity (anti-selectivity) to that by (E)-crotyl acetate at 60 ° C.