Synthesis of 2-aminobenzofurans via base-mediated [3 + 2] annulation of N-phenoxy amides with gem-difluoroalkenes

Organic Chemistry Frontiers, Год журнала: 2021, Номер 8(16), С. 4452 - 4458

Опубликована: Янв. 1, 2021

Efficient metal-free [3 + 2] annulation of N-phenoxy amides with gem-difluoroalkenes has been realized for the assembly 2-aminobenzofuran derivatives potent cytotoxicity against cancer cell lines and application potential DELs.

Язык: Английский

Vicinal stereocenters via asymmetric allylic alkylation and Cope rearrangement: a straightforward route to functionally and stereochemically rich heterocycles

Chemical Science, Год журнала: 2023, Номер 14(10), С. 2755 - 2762

Опубликована: Янв. 1, 2023

An asymmetric allylic alkylation/Cope rearrangement (AAA/[3,3]) capable of stereoselectively constructing vicinal stereocenters has been developed. Strategically integrated 4-methylation on the 3,3-dicyano-1,5-diene controls stereoselectivity and drives Cope equilibrium in forward direction. The AAA/[3,3] sequence rapidly converts abundant achiral racemic starting materials into valuable (hetero)cycloalkane building blocks bearing significant functional stereochemical complexity, highlighting value (hetero)cyclohexylidenemalononitriles as launching points for complex heterocycle synthesis. On this line, resulting alkylidenemalononitrile moiety can be readily converted amides via Hayashi-Lear amidation to ultimately yield amido-piperidines, tropanes, related scaffolds with 3-5 drug-like functionality.

Язык: Английский

Hydrogen bonding-promoted tunable approach for access to aza-bicyclo-[3.3.0]octanes and cyclopenta[b] pyrroles

Chemical Communications, Год журнала: 2024, Номер 60(37), С. 4922 - 4925

Опубликована: Янв. 1, 2024

A unified strategy is disclosed that builds on successfully engaging the aniline nitrogen of 1,3-amphoteric γ-aminocyclopentenone for a tandem annulation with electron-poor alkynes, solely assisted by H-bonding network HFIP.

Язык: Английский