Carbonyl group-assisted 1,3-amine addition to α,β-unsaturated aldehydes
An unusual 1,3-addition products were obtained when amines were reacted with α,β-unsaturated aldehydes compounds in the presence of iodine and an oxidant. The versatile unsaturated α-amino acetals are highly useful amino acid derivatives and can be converted to a wide variety of synthetically useful...
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sg-ntu-dr.10356-1806272024-10-18T15:32:13Z Carbonyl group-assisted 1,3-amine addition to α,β-unsaturated aldehydes Zhang, Zhenguo Ren, Mi Lu, Ming-Zhu Jia, Zhenhua Loh, Teck-Peng School of Chemistry, Chemical Engineering and Biotechnology Engineering Unsaturated α-amino acetals Iodine An unusual 1,3-addition products were obtained when amines were reacted with α,β-unsaturated aldehydes compounds in the presence of iodine and an oxidant. The versatile unsaturated α-amino acetals are highly useful amino acid derivatives and can be converted to a wide variety of synthetically useful building blocks. Various control experiments have shown that the reaction proceeded via a mechanism involving the formation of imine/enamine intermediates followed by a 1,2-amine group migration reaction. Agency for Science, Technology and Research (A*STAR) Nanyang Technological University We gratefully acknowledge the financial support from the Distinguished University Professor grant (Nanyang Technological University) and the Agency for Science, Technology, and Research (No. A*STAR) under its MTC Individual Research grant (No. M21K2c0114) and RIE2025 MTC Programmatic Fund (No. M22K9b0049) for T.P.L. 2024-10-15T06:53:39Z 2024-10-15T06:53:39Z 2024 Journal Article Zhang, Z., Ren, M., Lu, M., Jia, Z. & Loh, T. (2024). Carbonyl group-assisted 1,3-amine addition to α,β-unsaturated aldehydes. Green Synthesis and Catalysis. https://dx.doi.org/10.1016/j.gresc.2024.04.003 2666-5549 https://hdl.handle.net/10356/180627 10.1016/j.gresc.2024.04.003 2-s2.0-85200402957 en M21K2c0114 M22K9b0049 Green Synthesis and Catalysis © 2024 Fudan University. Publishing Services by Elsevier B.V. on behalf of KeAi Communications Co. Ltd. This is an open access article under the CC BYNC-ND license (http://creativecommons.org/licenses/by-nc-nd/4.0/). application/pdf |
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Engineering Unsaturated α-amino acetals Iodine |
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Engineering Unsaturated α-amino acetals Iodine Zhang, Zhenguo Ren, Mi Lu, Ming-Zhu Jia, Zhenhua Loh, Teck-Peng Carbonyl group-assisted 1,3-amine addition to α,β-unsaturated aldehydes |
| description |
An unusual 1,3-addition products were obtained when amines were reacted with α,β-unsaturated aldehydes compounds in the presence of iodine and an oxidant. The versatile unsaturated α-amino acetals are highly useful amino acid derivatives and can be converted to a wide variety of synthetically useful building blocks. Various control experiments have shown that the reaction proceeded via a mechanism involving the formation of imine/enamine intermediates followed by a 1,2-amine group migration reaction. |
| author2 |
School of Chemistry, Chemical Engineering and Biotechnology |
| author_facet |
School of Chemistry, Chemical Engineering and Biotechnology Zhang, Zhenguo Ren, Mi Lu, Ming-Zhu Jia, Zhenhua Loh, Teck-Peng |
| format |
Article |
| author |
Zhang, Zhenguo Ren, Mi Lu, Ming-Zhu Jia, Zhenhua Loh, Teck-Peng |
| author_sort |
Zhang, Zhenguo |
| title |
Carbonyl group-assisted 1,3-amine addition to α,β-unsaturated aldehydes |
| title_short |
Carbonyl group-assisted 1,3-amine addition to α,β-unsaturated aldehydes |
| title_full |
Carbonyl group-assisted 1,3-amine addition to α,β-unsaturated aldehydes |
| title_fullStr |
Carbonyl group-assisted 1,3-amine addition to α,β-unsaturated aldehydes |
| title_full_unstemmed |
Carbonyl group-assisted 1,3-amine addition to α,β-unsaturated aldehydes |
| title_sort |
carbonyl group-assisted 1,3-amine addition to α,β-unsaturated aldehydes |
| publishDate |
2024 |
| url |
https://hdl.handle.net/10356/180627 |
| _version_ |
1814777750156738560 |