Work

Stereocontrol in Conformationally Stable C(sp 2 )─C(sp 3 ) Atropisomers

Year: 2025

Type: article

Abstract: We report a two‐step sequence for the enantioselective construction of a rare family of stable C(sp 2 )─C(sp 3 ) 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 2 )─C(sp 3 ) bond, effectively locking and stabilizing its configuration.

Source: Angewandte Chemie International Edition

DOI: 10.1002/anie.202506810

Authors: Antoine Domain, Guishun Bai, Juan‐Carlos Castillo, Hassane Moussa Abdraman, Stéphane Humbel, Michel Giorgi, Jean‐Valère Naubron, Sara Chentouf, Jean Rodriguez, Xiaoze Bao, Damien Bonne

Institutions: Centre National de la Recherche Scientifique, Aix-Marseille Université, Centrale Méditerranée, Institut des Sciences Moléculaires de Marseille, Zhejiang University of Technology, Pedagogical and Technological University of Colombia, Fédération des Sciences Chimiques de Marseille

Language: English

Topic: Axial and Atropisomeric Chirality Synthesis

Subfield: Organic Chemistry

Field: Chemistry

Domain: Physical Sciences

Open Access status: hybrid

Estimated APC paid: $5,510

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

Awards: G2145608027, Combining Organocatalysis and Conversions of Chirality for the Control of Multiple Stereogenic Elements

OpenAlex ID: W4410709583

FWCI: 3.47

Cites: 67

Cited by: 12

Related to: 10