Enantioselective vinylogous-Mukaiyama-type dearomatisation by anion-binding catalysis

The first enantioselective vinylogous Mukaiyama-type dearomatisation of heteroarenes under anion-binding catalysis is presented. A recyclable tetrakistriazole catalyst was used for the enantiocontrol of the remote vinylogous active position of silyl dienol ethers. This approach provided chiral heterocycles bearing alpha,beta-unsaturated chains with complete regioselectivity and excellent enantioselectivities (up to 97.5 : 2.5 e.r.).

Automated summary

The study demonstrates the first enantioselective vinylogous Mukaiyama-type dearomatisation of heteroarenes under anion-binding catalysis, utilizing a recyclable tetrakistriazole catalyst for enantiocontrol of silyl dienol ethers. This approach results in chiral heterocycles with alpha,beta-unsaturated chains showing complete regioselectivity and excellent enantioselectivities (up to 97.5 : 2.5 e.r.).