Atroposelective Arene-Forming Alkene Metathesis

Jončev, Zlatko and Sparr, Christof. (2022) Atroposelective Arene-Forming Alkene Metathesis. Angewandte Chemie International Edition, 61 (51). e202211168.

PDF - Published Version
Available under License CC BY-NC (Attribution-NonCommercial).


Official URL: https://edoc.unibas.ch/90230/

Downloads: Statistics Overview


Alkene metathesis catalyzed by enantiopure metal alkylidene complexes enables exceptionally versatile strategies to products with configurationally-defined stereocenters. Desymmetriza-tion 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, stereo-selective 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.
Faculties and Departments:05 Faculty of Science > Departement Chemie > Chemie > Organische Chemie (Sparr)
UniBasel Contributors:Sparr, Christof
Item Type:Article, refereed
Article Subtype:Research Article
Note:Publication type according to Uni Basel Research Database: Journal article
Identification Number:
edoc DOI:
Last Modified:22 Dec 2022 08:17
Deposited On:22 Dec 2022 08:17

Repository Staff Only: item control page