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Issue 5, 2017
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Photoswitchable interlocked thiodiglycolamide as a cocatalyst of a chalcogeno-Baylis–Hillman reaction

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Abstract

En route to a photoswitchable interlocked catalyst we have proved the ability of thiodiglycolamide to act as a template in the formation of hydrogen-bonded [2]rotaxanes. X-ray diffraction studies reveal the shielding of the sulfide atom by the macrocycle. A series of molecular shuttles are described as having an isomerizable fumaramide and thiodiglycolamide binding sites for controlling the relative ring position at will. By employing these systems as photoregulated catalysts, the TiCl4-mediated chalcogeno-Morita–Baylis–Hillman reaction is tested. In the presence of the maleamide shuttle, in which the sulfide function is encapsulated by the macrocycle, a complete loss in control of the geometry of the produced aldol is observed. The E-aldol adduct is predominantly obtained when the photoisomerized fumaramide shuttle, in which the sulfide function is exposed, is used.

Graphical abstract: Photoswitchable interlocked thiodiglycolamide as a cocatalyst of a chalcogeno-Baylis–Hillman reaction

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Article information


Submitted
15 Feb 2017
Accepted
07 Mar 2017
First published
07 Mar 2017

This article is Open Access
All publication charges for this article have been paid for by the Royal Society of Chemistry

Chem. Sci., 2017,8, 3775-3780
Article type
Edge Article

Photoswitchable interlocked thiodiglycolamide as a cocatalyst of a chalcogeno-Baylis–Hillman reaction

A. Martinez-Cuezva, A. Saura-Sanmartin, T. Nicolas-Garcia, C. Navarro, R. Orenes, M. Alajarin and J. Berna, Chem. Sci., 2017, 8, 3775 DOI: 10.1039/C7SC00724H

This article is licensed under a Creative Commons Attribution 3.0 Unported Licence. You can use material from this article in other publications without requesting further permissions from the RSC, provided that the correct acknowledgement is given.

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