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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| Format: | Article |
| Language: | English |
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KeAi Communications Co. Ltd.
2025-05-01
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| Series: | Green Synthesis and Catalysis |
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| Online Access: | http://www.sciencedirect.com/science/article/pii/S2666554924000462 |
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| author | Zhenguo Zhang Mi Ren Ming-Zhu Lu Zhenhua Jia Teck-Peng Loh |
| author_facet | Zhenguo Zhang Mi Ren Ming-Zhu Lu Zhenhua Jia Teck-Peng Loh |
| author_sort | Zhenguo Zhang |
| collection | DOAJ |
| 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. |
| format | Article |
| id | doaj-art-e579a5a11c1c48cf8ef2a130c6a53e3d |
| institution | Matheson Library |
| issn | 2666-5549 |
| language | English |
| publishDate | 2025-05-01 |
| publisher | KeAi Communications Co. Ltd. |
| record_format | Article |
| series | Green Synthesis and Catalysis |
| spelling | doaj-art-e579a5a11c1c48cf8ef2a130c6a53e3d2025-07-04T04:47:04ZengKeAi Communications Co. Ltd.Green Synthesis and Catalysis2666-55492025-05-0162202205Carbonyl group-assisted 1,3-amine addition to α,β-unsaturated aldehydesZhenguo Zhang0Mi Ren1Ming-Zhu Lu2Zhenhua Jia3Teck-Peng Loh4College of Advanced Interdisciplinary Science and Technology, Henan University of Technology, Zhengzhou 450001, China; Division of Chemistry and Biological Chemistry, School of Chemistry Chemical Engineering & Biotechnology, Nanyang Technological University, 21 Nanyang Link 637371, SingaporeSchool of Chemistry and Molecular Engineering, Nanjing Tech University, Nanjing 211816, ChinaCollege of Advanced Interdisciplinary Science and Technology, Henan University of Technology, Zhengzhou 450001, ChinaCollege of Advanced Interdisciplinary Science and Technology, Henan University of Technology, Zhengzhou 450001, ChinaCollege of Advanced Interdisciplinary Science and Technology, Henan University of Technology, Zhengzhou 450001, China; Division of Chemistry and Biological Chemistry, School of Chemistry Chemical Engineering & Biotechnology, Nanyang Technological University, 21 Nanyang Link 637371, Singapore; School of Chemistry and Molecular Engineering, Nanjing Tech University, Nanjing 211816, China; Corresponding author.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.http://www.sciencedirect.com/science/article/pii/S26665549240004621,3-Amine additionα,β-Unsaturated aldehydes1,2-Amine group migrationUnsaturated α-amino acetalsIodine |
| spellingShingle | Zhenguo Zhang Mi Ren Ming-Zhu Lu Zhenhua Jia Teck-Peng Loh Carbonyl group-assisted 1,3-amine addition to α,β-unsaturated aldehydes Green Synthesis and Catalysis 1,3-Amine addition α,β-Unsaturated aldehydes 1,2-Amine group migration Unsaturated α-amino acetals Iodine |
| title | 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_short | 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 |
| topic | 1,3-Amine addition α,β-Unsaturated aldehydes 1,2-Amine group migration Unsaturated α-amino acetals Iodine |
| url | http://www.sciencedirect.com/science/article/pii/S2666554924000462 |
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