posted on 2024-03-20, 06:43authored byLian-Jie Li, Jun-Chun Zhang, Wei-Peng Li, Dan Zhang, Kaining Duanmu, Hui Yu, Qian Ping, Ze-Peng Yang
The catalytic and enantioselective
construction of quaternary
(all-carbon
substituents) stereocenters poses a formidable challenge in organic
synthesis due to the hindrance caused by steric factors. One conceptually
viable and potentially versatile approach is the coupling of a C–C
bond through an outer-sphere mechanism, accompanied by the realization
of enantiocontrol through cooperative catalysis; however, examples
of such processes are yet to be identified. Herein, we present such
a method for creating different compounds with quaternary stereocenters
by photoredox/Fe/chiral primary amine triple catalysis. This approach
facilitates the connection of an unactivated alkyl source with a tertiary
alkyl moiety, which is also rare. The scalable process exhibits mild
conditions, does not necessitate the use of a base, and possesses
a good functional-group tolerance. Preliminary investigations into
the underlying mechanisms have provided valuable insights into the
reaction pathway.