Ontology highlight
ABSTRACT:
SUBMITTER: Ashford MW
PROVIDER: S-EPMC7540707 | biostudies-literature | 2020 Sep
REPOSITORIES: biostudies-literature
Chemistry (Weinheim an der Bergstrasse, Germany) 20200818 53
A catalytic enantioselective synthesis of heterocyclic vicinal fluoroamines is reported. A chiral Brønsted acid promotes aza-Michael addition to fluoroalkenyl heterocycles to give a prochiral enamine intermediate that undergoes asymmetric protonation upon rearomatization. The reaction accommodates a range of azaheterocycles and nucleophiles, generating the C-F stereocentre in high enantioselectivity, and is also amenable to stereogenic C-CF<sub>3</sub> bonds. Extensive DFT calculations provided ...[more]