Asymmetric bicyclopentylation
The asymmetric synthesis of bicyclo[1.1.1]pentanes (BCPs) by the direct addition of radicals to the strained hydrocarbon [1.1.1]propellane has been reported by the Anderson and Duarte groups.
Published in Nature Communications, SBM CDT DPhil students Marie Wong and Alistair Sterling developed a multicatalytic approach that uses an organocatalyst, a photoredox catalyst, and a hydrogen atom transfer catalyst to enable the first asymmetric ring opening of [1.1.1]propellane. Displaying broad substrate scope, the theoretical basis for enantioselectivity reveals a complex balance of factors, including the unprecedented observation of organocatalyst-substrate non-covalent interactions. This work opens up new opportunities in medicinal chemistry for these fascinating phenyl bioisosteres.
