Synthesis of substituted γ- and δ-lactams through mannich-type reactions of solid-supported N -acyliminium ions
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 c...
| Main Authors: | , , , , , |
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| Other Authors: | |
| Format: | Journal Article |
| Language: | English |
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2015
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| Online Access: | https://hdl.handle.net/10356/107485 http://hdl.handle.net/10220/25576 http://dx.doi.org/10.1002/ejoc.201500054 |
| _version_ | 1811677845818179584 |
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| author | Komnatnyy, Vitaly V. Taveras, Kennedy M. Nandurkar, Nitin S. Le Quement, Sebastian T. Givskov, Michael Nielsen, Thomas Eiland |
| author2 | Singapore Centre for Environmental Life Sciences Engineering |
| author_facet | Singapore Centre for Environmental Life Sciences Engineering Komnatnyy, Vitaly V. Taveras, Kennedy M. Nandurkar, Nitin S. Le Quement, Sebastian T. Givskov, Michael Nielsen, Thomas Eiland |
| author_sort | Komnatnyy, Vitaly V. |
| collection | NTU |
| description | 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 %). |
| first_indexed | 2024-10-01T02:43:51Z |
| format | Journal Article |
| id | ntu-10356/107485 |
| institution | Nanyang Technological University |
| language | English |
| last_indexed | 2024-10-01T02:43:51Z |
| publishDate | 2015 |
| record_format | dspace |
| spelling | ntu-10356/1074852019-12-06T22:32:12Z Synthesis of substituted γ- and δ-lactams through mannich-type reactions of solid-supported N -acyliminium ions Komnatnyy, Vitaly V. Taveras, Kennedy M. Nandurkar, Nitin S. Le Quement, Sebastian T. Givskov, Michael Nielsen, Thomas Eiland Singapore Centre for Environmental Life Sciences Engineering DRNTU::Science::Chemistry::Organic chemistry 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 %). 2015-05-18T05:01:05Z 2019-12-06T22:32:12Z 2015-05-18T05:01:05Z 2019-12-06T22:32:12Z 2015 2015 Journal Article 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. 1434-193X https://hdl.handle.net/10356/107485 http://hdl.handle.net/10220/25576 http://dx.doi.org/10.1002/ejoc.201500054 en European journal of organic chemistry © 2015 WILEY-VCH Verlag GmbH & Co. KGaA, Weinheim. |
| spellingShingle | DRNTU::Science::Chemistry::Organic chemistry Komnatnyy, Vitaly V. Taveras, Kennedy M. Nandurkar, Nitin S. Le Quement, Sebastian T. Givskov, Michael Nielsen, Thomas Eiland Synthesis of substituted γ- and δ-lactams through mannich-type reactions of solid-supported N -acyliminium ions |
| title | Synthesis of substituted γ- and δ-lactams through mannich-type reactions of solid-supported N -acyliminium ions |
| title_full | Synthesis of substituted γ- and δ-lactams through mannich-type reactions of solid-supported N -acyliminium ions |
| title_fullStr | Synthesis of substituted γ- and δ-lactams through mannich-type reactions of solid-supported N -acyliminium ions |
| title_full_unstemmed | Synthesis of substituted γ- and δ-lactams through mannich-type reactions of solid-supported N -acyliminium ions |
| title_short | Synthesis of substituted γ- and δ-lactams through mannich-type reactions of solid-supported N -acyliminium ions |
| title_sort | synthesis of substituted γ and δ lactams through mannich type reactions of solid supported n acyliminium ions |
| topic | DRNTU::Science::Chemistry::Organic chemistry |
| url | https://hdl.handle.net/10356/107485 http://hdl.handle.net/10220/25576 http://dx.doi.org/10.1002/ejoc.201500054 |
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