Atroposelective arene-forming alkene metathesis

21 March 2022, Version 1
This content is a preprint and has not undergone peer review at the time of posting.


Alkene metathesis catalysed by enantiopure metal alkylidene complexes enables versatile strategies to products with configurationally-defined stereocentres. Desymmetrisation processes thereby provide particularly 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 high yields and enantioselectivities of up to 98:2 e.r. As the disconnection of each bond of aromatic products 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.


Stereoselective Catalysis
Arene Formation
Conformational Analysis

Supplementary materials

Supplementary Materials
Experimental details, supplementary methods, NMR spectra and crystallographic data.


Comments are not moderated before they are posted, but they can be removed by the site moderators if they are found to be in contravention of our Commenting Policy [opens in a new tab] - please read this policy before you post. Comments should be used for scholarly discussion of the content in question. You can find more information about how to use the commenting feature here [opens in a new tab] .
This site is protected by reCAPTCHA and the Google Privacy Policy [opens in a new tab] and Terms of Service [opens in a new tab] apply.