Real-Time Control of the Enantioselectivity of a Supramolecular Catalyst Allows Selecting the Configuration of Consecutively Formed Stereogenic Centers - Sorbonne Université Access content directly
Journal Articles Angewandte Chemie Year : 2017

Real-Time Control of the Enantioselectivity of a Supramolecular Catalyst Allows Selecting the Configuration of Consecutively Formed Stereogenic Centers

Abstract

The enantiomeric state of a supramolecular copper catalyst can be switched in situ in ca. five seconds. The dynamic property of the catalyst is provided by the non-covalent nature of the helical assemblies supporting the copper centers. These assemblies are formed by mixing an achiral benzene-1,3,5-tricarboxamide (BTA) phosphine ligand (for copper coordination) and both enantiomers of a chiral phosphine-free BTA co-monomer (for chirality amplification). The enantioselectivity of the hydrosilylation reaction is fixed by the BTA enantiomer in excess, which can be altered by simple BTA addition. As a result of the complete and fast stereochemical switch, any combination of the enantiomers was obtained during the conversion of a mixture of two substrates.
Fichier principal
Vignette du fichier
Zimbron_Real-time_control.pdf (2.39 Mo) Télécharger le fichier
Origin Files produced by the author(s)
Loading...

Dates and versions

hal-01611679 , version 1 (06-10-2017)

Identifiers

Cite

Jeremy M Zimbron, Xavier Caumes, Yan Li, Christophe M Thomas, Matthieu Raynal, et al.. Real-Time Control of the Enantioselectivity of a Supramolecular Catalyst Allows Selecting the Configuration of Consecutively Formed Stereogenic Centers. Angewandte Chemie, 2017, ⟨10.1002/ange.201706757⟩. ⟨hal-01611679⟩
117 View
162 Download

Altmetric

Share

Gmail Mastodon Facebook X LinkedIn More