Zhenguo Zhang, Mi Ren, Ming-Zhu Lu, Zhenhua Jia, Teck-Peng Loh
{"title":"Carbonyl group-assisted 1,3-amine addition to α,β-unsaturated aldehydes","authors":"Zhenguo Zhang, Mi Ren, Ming-Zhu Lu, Zhenhua Jia, Teck-Peng Loh","doi":"10.1016/j.gresc.2024.04.003","DOIUrl":null,"url":null,"abstract":"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.","PeriodicalId":12794,"journal":{"name":"Green Synthesis and Catalysis","volume":"38 1","pages":""},"PeriodicalIF":0.0000,"publicationDate":"2024-04-29","publicationTypes":"Journal Article","fieldsOfStudy":null,"isOpenAccess":false,"openAccessPdf":"","citationCount":"0","resultStr":null,"platform":"Semanticscholar","paperid":null,"PeriodicalName":"Green Synthesis and Catalysis","FirstCategoryId":"1085","ListUrlMain":"https://doi.org/10.1016/j.gresc.2024.04.003","RegionNum":0,"RegionCategory":null,"ArticlePicture":[],"TitleCN":null,"AbstractTextCN":null,"PMCID":null,"EPubDate":"","PubModel":"","JCR":"","JCRName":"","Score":null,"Total":0}
引用次数: 0
Abstract
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.