Issue 27, 2018

Selective activation of organocatalysts by specific signals

Abstract

Reminiscent of signal transduction in biological systems, artificial catalysts whose activity can be controlled by physical or chemical signals would be of high interest in the design of chemical systems that can respond to their environment. Self-immolative chemistry offers a generic method for the development of catalysts that can be activated by different signals. To demonstrate the versatility of that concept, we synthesized organocatalysts that can be activated by three different signals and that can be used to control two different reactions. In this way the organocatalyst proline is designed as a pro-catalyst that is activated either by the chemical signal H2O2, by light or by the enzyme penicillin acylase. The pro-catalysts were used to exert temporal control over the rate of an aldol reaction and a Michael reaction.

Graphical abstract: Selective activation of organocatalysts by specific signals

Supplementary files

Article information

Article type
Edge Article
Submitted
04 may 2018
Accepted
19 iyn 2018
First published
20 iyn 2018
This article is Open Access

All publication charges for this article have been paid for by the Royal Society of Chemistry
Creative Commons BY-NC license

Chem. Sci., 2018,9, 5999-6005

Selective activation of organocatalysts by specific signals

C. Maity, F. Trausel and R. Eelkema, Chem. Sci., 2018, 9, 5999 DOI: 10.1039/C8SC02019A

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