Reimagining Enantioselective Aminoalcohol Synthesis via Chemoselective Electrocatalytic Radical Cross Couplings

Aminoalcohols are expressed in natural products, blockbuster pharmaceuticals, agrochemicals, and key building blocks for innumerable society-benefitting applications. Historically their synthesis relies on polar-bond retrosynthetic analysis and often suffers from extensive protecting/functional group manipulation chemistry that hinders their direct access. Here we show how a simple serine-derived chemical cassette can be leveraged in a series of electrocatalytic transformations to dramatically simplify the way such structures can be made enantio- and chemoselectively in a modular fashion. This chemistry can be used to rapidly create libraries of useful building blocks and the radical retrosynthetic logic employed can be applied to truncate the synthesis of known structures. This methodology can be used on large scale as well as demonstrated with a unique flow reactor setup.