Ferenc Miklós , Kristóf Bozó , Zsolt Galla , Matti Haukka , Ferenc Fülöp
{"title":"降冰片烯β-氨基酸到嘧啶[2,1-a]异吲哚对映体的无迹手性转移","authors":"Ferenc Miklós , Kristóf Bozó , Zsolt Galla , Matti Haukka , Ferenc Fülöp","doi":"10.1016/j.tetasy.2017.07.006","DOIUrl":null,"url":null,"abstract":"<div><p><span>The synthesis of two enantiomeric pairs of pyrimidoisoindoles </span><strong>9a</strong>, <strong>9b</strong> and <strong>10a</strong>, <span>10b</span><span> is reported. During a domino ring-closure reaction, followed by cycloreversion<span>, the chirality of </span></span><em>diendo</em>-(−)-(1<em>R</em>,2<em>S</em>,3<em>R</em>,4<em>S</em>)-3-aminobicyclo[2.2.1]hept-5-ene-2-carboxamide [(−)-<strong>1</strong>] was successfully transfered to heterocycles (+)-<strong>9a</strong>, (+)-<strong>10a</strong>, (−)-<strong>9b</strong>, (−)-<strong>10b</strong> and (−)-<strong>10c</strong>.</p></div>","PeriodicalId":22237,"journal":{"name":"Tetrahedron, asymmetry","volume":"28 10","pages":"Pages 1401-1406"},"PeriodicalIF":0.0000,"publicationDate":"2017-10-15","publicationTypes":"Journal Article","fieldsOfStudy":null,"isOpenAccess":false,"openAccessPdf":"https://sci-hub-pdf.com/10.1016/j.tetasy.2017.07.006","citationCount":"5","resultStr":"{\"title\":\"Traceless chirality transfer from a norbornene β-amino acid to pyrimido[2,1-a]isoindole enantiomers\",\"authors\":\"Ferenc Miklós , Kristóf Bozó , Zsolt Galla , Matti Haukka , Ferenc Fülöp\",\"doi\":\"10.1016/j.tetasy.2017.07.006\",\"DOIUrl\":null,\"url\":null,\"abstract\":\"<div><p><span>The synthesis of two enantiomeric pairs of pyrimidoisoindoles </span><strong>9a</strong>, <strong>9b</strong> and <strong>10a</strong>, <span>10b</span><span> is reported. During a domino ring-closure reaction, followed by cycloreversion<span>, the chirality of </span></span><em>diendo</em>-(−)-(1<em>R</em>,2<em>S</em>,3<em>R</em>,4<em>S</em>)-3-aminobicyclo[2.2.1]hept-5-ene-2-carboxamide [(−)-<strong>1</strong>] was successfully transfered to heterocycles (+)-<strong>9a</strong>, (+)-<strong>10a</strong>, (−)-<strong>9b</strong>, (−)-<strong>10b</strong> and (−)-<strong>10c</strong>.</p></div>\",\"PeriodicalId\":22237,\"journal\":{\"name\":\"Tetrahedron, asymmetry\",\"volume\":\"28 10\",\"pages\":\"Pages 1401-1406\"},\"PeriodicalIF\":0.0000,\"publicationDate\":\"2017-10-15\",\"publicationTypes\":\"Journal Article\",\"fieldsOfStudy\":null,\"isOpenAccess\":false,\"openAccessPdf\":\"https://sci-hub-pdf.com/10.1016/j.tetasy.2017.07.006\",\"citationCount\":\"5\",\"resultStr\":null,\"platform\":\"Semanticscholar\",\"paperid\":null,\"PeriodicalName\":\"Tetrahedron, asymmetry\",\"FirstCategoryId\":\"1085\",\"ListUrlMain\":\"https://www.sciencedirect.com/science/article/pii/S0957416617302653\",\"RegionNum\":0,\"RegionCategory\":null,\"ArticlePicture\":[],\"TitleCN\":null,\"AbstractTextCN\":null,\"PMCID\":null,\"EPubDate\":\"\",\"PubModel\":\"\",\"JCR\":\"Q2\",\"JCRName\":\"Chemistry\",\"Score\":null,\"Total\":0}","platform":"Semanticscholar","paperid":null,"PeriodicalName":"Tetrahedron, asymmetry","FirstCategoryId":"1085","ListUrlMain":"https://www.sciencedirect.com/science/article/pii/S0957416617302653","RegionNum":0,"RegionCategory":null,"ArticlePicture":[],"TitleCN":null,"AbstractTextCN":null,"PMCID":null,"EPubDate":"","PubModel":"","JCR":"Q2","JCRName":"Chemistry","Score":null,"Total":0}
Traceless chirality transfer from a norbornene β-amino acid to pyrimido[2,1-a]isoindole enantiomers
The synthesis of two enantiomeric pairs of pyrimidoisoindoles 9a, 9b and 10a, 10b is reported. During a domino ring-closure reaction, followed by cycloreversion, the chirality of diendo-(−)-(1R,2S,3R,4S)-3-aminobicyclo[2.2.1]hept-5-ene-2-carboxamide [(−)-1] was successfully transfered to heterocycles (+)-9a, (+)-10a, (−)-9b, (−)-10b and (−)-10c.
期刊介绍:
Cessation. Tetrahedron: Asymmetry presents experimental or theoretical research results of outstanding significance and timeliness on asymmetry in organic, inorganic, organometallic and physical chemistry, as well as its application to related disciplines, especially bio-organic chemistry.
The journal publishes critical reviews, original research articles and preliminary communications dealing with all aspects of the chemical, physical and theoretical properties of non-racemic organic and inorganic materials and processes. Topics relevant to the journal include: the physico-chemical and biological properties of enantiomers; strategies and methodologies of asymmetric synthesis; resolution; chirality recognition and enhancement; analytical techniques for assessing enantiomeric purity and the unambiguous determination of absolute configuration; and molecular graphics and modelling methods for interpreting and predicting asymmetric phenomena. Papers describing the synthesis or properties of non-racemic molecules will be required to include a separate statement in the form of a Stereochemistry Abstract, for publication in the same issue, of the criteria used for the assignment of configuration and enantiomeric purity.