ArticleAngewandte Chemie (International ed. in English)2022
Atroposelective Arene-Forming Alkene Metathesis.
Article in Angewandte Chemie (International ed. in English), 2022. The graph could read no effect estimate from its abstract, so it casts no vote on the map. Cited by 3 papers.
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Who cites it
3 citing papers in PubMed.
- Aromatic ring-opening metathesis.Nature · 2025Article
- Application of Olefin Metathesis in the Synthesis of Carbo- and Heteroaromatic Compounds-Recent Advances.Molecules (Basel, Switzerland) · 2023Review
- Atroposelective Arene-Forming Alkene Metathesis.Angewandte Chemie (International ed. in English) · 2022Article
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Authors and funding
2 authors.
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Abstract
Alkene metathesis catalyzed by enantiopure metal alkylidene complexes enables exceptionally versatile strategies to products with configurationally-defined stereocenters. Desymmetrization processes thereby provide reliable stereoselective routes to aliphatic structures, while the differentiation of aromatic stereogenic units remained an outstanding challenge. Herein, we describe the feasibility of alkene metathesis to catalytically control stereogenic axes by traceless arene formation. Stereodynamic trienes are selectively converted into corresponding binaphthalene atropisomers upon exposure to a chiral molybdenum catalyst. Remarkably, stereoselective arene-forming metathesis allows enantioselectivities of up to 98 : 2 e.r. and excellent yields. As the disconnection of each bond of an aromatic target is retrosynthetically conceivable, it is anticipated that forging arenes by means of stereoselective metathesis will enable versatile approaches for the synthesis of a broad range of molecular topologies with precisely defined configuration.
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