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Title: Synthesis of substituted γ- and δ-lactams through mannich-type reactions of solid-supported N -acyliminium ions
Authors: Komnatnyy, Vitaly V.
Taveras, Kennedy M.
Nandurkar, Nitin S.
Le Quement, Sebastian T.
Givskov, Michael
Nielsen, Thomas Eiland
Keywords: DRNTU::Science::Chemistry::Organic chemistry
Issue Date: 2015
Source: Komnatnyy, V. V., Taveras, K. M., Nandurkar, N. S., Le Quement, S. T., Givskov, M., & Nielsen, T. E. (2015). Synthesis of substituted γ- and δ-lactams through mannich-type reactions of solid-supported N -acyliminium ions. European journal of organic chemistry, 2015(16), 3524-3530.
Series/Report no.: European journal of organic chemistry
Abstract: We report the results of our recent investigations into the reactivity of cyclic solid-supported N-acyliminium ions. An intermolecular Mannich-type transformation of these intermediates was used to generate libraries of substituted lactams. Masked aldehyde building blocks were readily prepared and coupled to peptides immobilized on PEGA800(polyethylene glycol dimethyl acrylamide) resin through an HMBA [4-(hydroxymethyl)benzoic acid] linker. When treated with acid, the aldehyde was cleanly released and condensed with the amide backbone to form a hydroxylactam/N-acyliminium ion, which underwent intermolecular reactions with a series of nucleophilic heterocycles, such as substituted indoles, thiophenes, furans, and electron-rich benzenes. The resulting lactams were formed within a few minutes and in high purities (typically >85 %).
ISSN: 1434-193X
DOI: 10.1002/ejoc.201500054
Rights: © 2015 WILEY-VCH Verlag GmbH & Co. KGaA, Weinheim.
Fulltext Permission: none
Fulltext Availability: No Fulltext
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