Work

Enantioselective Synthesis of Benzodihydrofurans Bearing Axial and Central Stereogenic Elements

Year: 2024

Type: article

Abstract: The enantioselective synthesis of chiral compounds containing multiple stereogenic elements via a single catalytic step is a challenging process. In the presence of α-chloronitrostyrenes and a chiral squaramide catalyst, C-C or C-N pro-axially chiral 2-naphthol substrates, featuring low barriers to enantiomerization, underwent a remote diastereo- and enantioselective domino Michael/O-alkylation. It provided the desired benzodihydrofurans bearing two stereogenic carbon atoms and a configurationally stable C-C or a C-N bond, thanks to a high increase of the barrier to rotation upon dihydrofurannulation.

Source: Chemistry - A European Journal

DOI: 10.1002/chem.202403374

Authors: Antoine Domain, Xiaoze Bao, Jean Rodriguez, Damien Bonne

Institutions: Centre National de la Recherche Scientifique, Aix-Marseille Université, Centrale Méditerranée, Institut des Sciences Moléculaires de Marseille, Zhejiang University of Technology

Language: English

Topic: Asymmetric Synthesis and Catalysis

Subfield: Organic Chemistry

Field: Chemistry

Domain: Physical Sciences

Open Access status: hybrid

Estimated APC paid: $4,640

Funders: Aix-Marseille Université, Agence Nationale de la Recherche, Centre National de la Recherche Scientifique