The stereoselective construction of fluorine-containing quaternary center is a synthetically challenging task. We reported a novel stereodivergent synthesis of fluorinated lactams bearing vicinal C-F quaternary and tertiary center via sequential approach. A facile solvent changing under mild condition induced fluorine stereoselective switching was directed by hydrogen-bonding effect, both syn- and anti- diastereomers were obtained in excellent results (dr &gt;20:1 and ee &gt;99%). The mechanism of desymmetrization process on fluorine-containing quaternary center was elucidated via DFT calculation. The usefulness of the fluorinated lactam synthon was proved by total synthesis of natural product analogues and fluorinated central nervous system drug study.

Hydrogen-bonding effect directed stereodivergent synthesis of lactams bearing vicinal tertiary and fluorine-containing quaternary stereogenic centers via sequential approach

Macromolecular Chemistry: The Second Century

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ACS Spring 2020 National Meeting & Expo

The official archive and repository for all ACS Meetings & Expositions abstracts and select posters or presentations.