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Revealing the Similarities of α,β-Unsaturated Iminiums and Acylazoliums in Organocatalysis

Ghosh, A and Biju, AT (2020) Revealing the Similarities of α,β-Unsaturated Iminiums and Acylazoliums in Organocatalysis. In: Angewandte Chemie - International Edition .

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Official URL: https://doi.org/10.1002/anie.202012581


The secondary amine-catalyzed reactions proceeding via α,β-unsaturated iminiums and the N-heterocyclic carbene (NHC)-catalyzed transformations taking place via α,β-unsaturated acylazoliums are the two widely used electrophilic intermediates in organocatalysis. Over the last two decades, these two intermediates are extensively utilized for the enantioselective construction of valuable molecules. Both intermediates are generated by the covalent binding of catalysts to the substrates leading to LUMO activation of α,β-unsaturated carbonyls. A variety of soft nucleophiles are known to add to the α,β-unsaturated iminiums and acylazoliums in a conjugate fashion, and in many cases, striking similarity in reactivity has been observed. Having said this, there are few cases where these intermediates exhibit difference in reactivity. This Minireview is aimed at highlighting the resemblances in reactivity between α,β-unsaturated iminiums and acylazoliums thereby shedding light on the unnoticed parallels of the two intermediates in organocatalysis. © 2020 Wiley-VCH GmbH

Item Type: Journal Article
Publication: Angewandte Chemie - International Edition
Publisher: Wiley-VCH Verlag
Additional Information: The copyright for this article belongs to Wiley-VCH Verlag
Keywords: Amines; Rate constants; Reaction intermediates, Catalyzed reactions; Covalent binding; Enantioselective construction; N-heterocyclic carbenes; Organocatalysis; Secondary amines; Shedding light, Catalysis
Department/Centre: Division of Chemical Sciences > Organic Chemistry
Date Deposited: 23 Mar 2021 10:20
Last Modified: 23 Mar 2021 10:20
URI: http://eprints.iisc.ac.in/id/eprint/68410

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