Enantioselective radical C-H amination for the synthesis of β-amino alcohols.

ABSTRACT: Asymmetric, radical C-H functionalizations are rare but powerful tools for solving modern synthetic challenges. Specifically, the enantio- and regioselective C-H amination of alcohols to access medicinally valuable chiral β-amino alcohols remains elusive. To solve this challenge, a radical relay chaperone strategy was designed, wherein an alcohol was transiently converted to an imidate radical that underwent intramolecular H-atom transfer (HAT). This regioselective HAT was also rendered enantioselective by harnessing energy transfer catalysis to mediate selective radical generation and interception by a chiral copper catalyst. The successful development of this multi-catalytic, asymmetric, radical C-H amination enabled broad access to chiral β-amino alcohols from a variety of alcohols cont

SUBMITTER: Nakafuku KM 

PROVIDER: S-EPMC7390680 | biostudies-literature | 2020 Aug

REPOSITORIES: biostudies-literature