Stereocontrol in Conformationally Stable C(sp <sup>2</sup> )─C(sp <sup>3</sup> ) Atropisomers
We report a two-step sequence for the enantioselective construction of a rare family of stable C(sp<sup>2</sup>)─C(sp<sup>3</sup>) atropisomers featuring two additional stereogenic centers. The process begins with an organocatalyzed dihydrobenzofurannulation that establishes and controls the stereochemistry of two carbon centers, followed by a highly diastereoselective functionalization that significantly enhances the barrier to diastereomerization of the C(sp<sup>2</sup>)─C(sp<sup>3</sup>) bond, effectively locking and stabilizing its configuration.
Authors
- Sara Chentouf (ORCID: https://orcid.org/0000-0003-0695-7260)
- Damien Bonne (ORCID: https://orcid.org/0000-0003-4479-4626)
- Xinhe Bao (ORCID: https://orcid.org/0000-0001-9404-6429)
- Michel Giorgi (ORCID: https://orcid.org/0000-0002-4367-1985)
- Jean‐Valère Naubron (ORCID: https://orcid.org/0000-0002-8523-4476)
- Juan‐Carlos Castillo (ORCID: https://orcid.org/0000-0002-6060-2578)
- Guishun Bai
- Stéphane Humbel (ORCID: https://orcid.org/0000-0001-5405-1848)
- Antoine Domain
- Jean Rodríguez
- Hassane Moussa Abdraman
Institutions
- Centre National de la Recherche Scientifique (FR)
- Aix-Marseille Université (FR)
- Pedagogical and Technological University of Colombia (CO)
- Centrale Méditerranée (FR)
- Zhejiang University of Technology (CN)
Publication Details
- Journal
- Angewandte Chemie International Edition
- Published
- 2025-05-24
- DOI
- https://doi.org/10.1002/anie.202506810
- Citations
- 6
- Primary Topic
- Axial and Atropisomeric Chirality Synthesis
- Type
- article
- Field-Weighted Citation Impact
- 5.62
Funders
- Aix-Marseille Université
- Universidad Pedagógica y Tecnológica de Colombia
- Agence Nationale de la Recherche
- National Natural Science Foundation of China
- Centre National de la Recherche Scientifique
- Natural Science Foundation for Young Scientists of Shanxi Province
- Young Scientists Fund