Dual-Face Nucleoside Scaffold Featuring a Stereogenic All-Carbon Quaternary Center. Intramolecular Silicon Tethered Group-Transfer Reaction

The design of a novel
nucleoside scaffold that exhibits an all-carbon
quaternary center is reported. This allows for both α- and β-anomers
of a given 2′-deoxy-2′,2′-difluoro nucleoside
analog (NA) to have potential biological activity. Using an intramolecular
atom-transfer reaction, an all-carbon quaternary center was obtained
without the use of heavy metals and/or harsh conditions. The chemistry
developed is efficient, easily scalable and leads to novel libraries
of molecules.