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Issue 4, 2014
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Towards a sustainable synthesis of aniline-derived amides using an indirect chemoenzymatic process: challenges and successes

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Abstract

A general, catalytic and sustainable synthesis of amides has been targeted which utilises a chemoenzymatic step to generate an activated amide coupling partner in situ. A screen of a series of known activating agents was performed and the successful agents taken forward to determine their utility in such a one-pot enzyme-catalysed process. In these studies, a new chemoselective reagent ((isopropylideneamino) 2-phenylacetate) has been identified, which demonstrates excellent selectivity for the acylation of primary anilines over secondary anilines, unlike the more conventional acid chloride equivalent, which is unselective. The development of a chemoenzymatic synthesis of 2-hydroxyethyl benzoates (ethylene glycol mono-benzoate esters) has also been achieved.

Graphical abstract: Towards a sustainable synthesis of aniline-derived amides using an indirect chemoenzymatic process: challenges and successes

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Publication details

The article was received on 07 Oct 2013, accepted on 18 Nov 2013 and first published on 02 Dec 2013


Article type: Paper
DOI: 10.1039/C3RA46499G
RSC Adv., 2014,4, 1609-1615

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    Towards a sustainable synthesis of aniline-derived amides using an indirect chemoenzymatic process: challenges and successes

    S. Lal and T. J. Snape, RSC Adv., 2014, 4, 1609
    DOI: 10.1039/C3RA46499G

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