Palladium-catalyzed enantioselective domino ring-opening/Hiyama coupling of cyclobutanones: development and application to the synthesis of (+)-herbertene-1,14-diol

We report a palladium-catalyzed enantioselective domino ring-opening/Hiyama coupling of cyclobutanones with alkenyl-[2-(hydroxymethyl)phenyl]dimethylsilanes, providing 1-indanones bearing a versatile alkenyl group and an all-carbon quaternary center. Our methodology was utilized as the key step in the asymmetric total synthesis of (+)-herbertene-1,14-diol.

Automated summary

We report a palladium-catalyzed reaction that enables the domino ring-opening/Hiyama coupling of cyclobutanones with alkenyl-[2-(hydroxymethyl)phenyl]dimethylsilanes. This reaction leads to the synthesis of 1-indanones bearing a versatile alkenyl group and an all-carbon quaternary center, which is of great significance in the synthesis of specific organic compounds.