{"title":"通过还原胺化优化立体选择性和可扩展的五元环反式-β-氨基酸构建模块的合成","authors":"Jungwoo Hong, Wonchul Lee, Hee-Seung Lee","doi":"10.1002/bkcs.12786","DOIUrl":null,"url":null,"abstract":"<p>We present an optimized method for the stereoselective synthesis of five-membered alicyclic and heterocyclic <i>trans</i>-β-amino acid derivatives. The process involves a reductive amination of β-keto esters using chiral auxiliary amines, with formic acid acting as a facilitator for rapid, diastereoselective reductions under gentle conditions. Our approach notably enhances isolated yields and permits the scalable production of <i>trans</i>-2-aminocyclopentanecarboxylic acid (<i>trans</i>-ACPC), 4-aminopyrrolidine-3-carboxylic acid (<i>trans</i>-APC), 4-aminotetrahydrofuran-3-carboxylic acid (<i>trans</i>-ATFC), and 4-aminotetrahydrothiophene-3-carboxylic acid (<i>trans</i>-ATTC) building blocks.</p>","PeriodicalId":54252,"journal":{"name":"Bulletin of the Korean Chemical Society","volume":null,"pages":null},"PeriodicalIF":1.7000,"publicationDate":"2023-10-30","publicationTypes":"Journal Article","fieldsOfStudy":null,"isOpenAccess":false,"openAccessPdf":"","citationCount":"0","resultStr":"{\"title\":\"Optimized stereoselective and scalable synthesis of five-membered cyclic trans-β-amino acid building blocks via reductive amination\",\"authors\":\"Jungwoo Hong, Wonchul Lee, Hee-Seung Lee\",\"doi\":\"10.1002/bkcs.12786\",\"DOIUrl\":null,\"url\":null,\"abstract\":\"<p>We present an optimized method for the stereoselective synthesis of five-membered alicyclic and heterocyclic <i>trans</i>-β-amino acid derivatives. The process involves a reductive amination of β-keto esters using chiral auxiliary amines, with formic acid acting as a facilitator for rapid, diastereoselective reductions under gentle conditions. Our approach notably enhances isolated yields and permits the scalable production of <i>trans</i>-2-aminocyclopentanecarboxylic acid (<i>trans</i>-ACPC), 4-aminopyrrolidine-3-carboxylic acid (<i>trans</i>-APC), 4-aminotetrahydrofuran-3-carboxylic acid (<i>trans</i>-ATFC), and 4-aminotetrahydrothiophene-3-carboxylic acid (<i>trans</i>-ATTC) building blocks.</p>\",\"PeriodicalId\":54252,\"journal\":{\"name\":\"Bulletin of the Korean Chemical Society\",\"volume\":null,\"pages\":null},\"PeriodicalIF\":1.7000,\"publicationDate\":\"2023-10-30\",\"publicationTypes\":\"Journal Article\",\"fieldsOfStudy\":null,\"isOpenAccess\":false,\"openAccessPdf\":\"\",\"citationCount\":\"0\",\"resultStr\":null,\"platform\":\"Semanticscholar\",\"paperid\":null,\"PeriodicalName\":\"Bulletin of the Korean Chemical Society\",\"FirstCategoryId\":\"92\",\"ListUrlMain\":\"https://onlinelibrary.wiley.com/doi/10.1002/bkcs.12786\",\"RegionNum\":4,\"RegionCategory\":\"化学\",\"ArticlePicture\":[],\"TitleCN\":null,\"AbstractTextCN\":null,\"PMCID\":null,\"EPubDate\":\"\",\"PubModel\":\"\",\"JCR\":\"\",\"JCRName\":\"\",\"Score\":null,\"Total\":0}","platform":"Semanticscholar","paperid":null,"PeriodicalName":"Bulletin of the Korean Chemical Society","FirstCategoryId":"92","ListUrlMain":"https://onlinelibrary.wiley.com/doi/10.1002/bkcs.12786","RegionNum":4,"RegionCategory":"化学","ArticlePicture":[],"TitleCN":null,"AbstractTextCN":null,"PMCID":null,"EPubDate":"","PubModel":"","JCR":"","JCRName":"","Score":null,"Total":0}
Optimized stereoselective and scalable synthesis of five-membered cyclic trans-β-amino acid building blocks via reductive amination
We present an optimized method for the stereoselective synthesis of five-membered alicyclic and heterocyclic trans-β-amino acid derivatives. The process involves a reductive amination of β-keto esters using chiral auxiliary amines, with formic acid acting as a facilitator for rapid, diastereoselective reductions under gentle conditions. Our approach notably enhances isolated yields and permits the scalable production of trans-2-aminocyclopentanecarboxylic acid (trans-ACPC), 4-aminopyrrolidine-3-carboxylic acid (trans-APC), 4-aminotetrahydrofuran-3-carboxylic acid (trans-ATFC), and 4-aminotetrahydrothiophene-3-carboxylic acid (trans-ATTC) building blocks.
期刊介绍：
The Bulletin of the Korean Chemical Society is an official research journal of the Korean Chemical Society. It was founded in 1980 and reaches out to the chemical community worldwide. It is strictly peer-reviewed and welcomes Accounts, Communications, Articles, and Notes written in English. The scope of the journal covers all major areas of chemistry: analytical chemistry, electrochemistry, industrial chemistry, inorganic chemistry, life-science chemistry, macromolecular chemistry, organic synthesis, non-synthetic organic chemistry, physical chemistry, and materials chemistry.
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