Péter Bagi, Kinga Juhász, Mihály Kállay, Dóra Hessz, Miklós Kubinyi, Elemér Fogassy, György Keglevich
{"title":"通过形成非对映体配合物制备对映纯1-异戊基-3-甲基-3-磷烯- 1-氧化物","authors":"Péter Bagi, Kinga Juhász, Mihály Kállay, Dóra Hessz, Miklós Kubinyi, Elemér Fogassy, György Keglevich","doi":"10.1002/hc.21411","DOIUrl":null,"url":null,"abstract":"<p>The resolution of 1-isopentyl-3-methyl-3-phospholene 1-oxide via the formation of diastereomeric complexes using TADDOL derivatives or the Ca<sup>2+</sup>-salts of tartaric acid derivatives was studied. Both enantiomers of the 1-isopentyl-3-phospholene oxide were prepared in an enantiopure form with (<i>R</i>,<i>R</i>)-spiro-TADDOL, or with the acidic Ca<sup>2+</sup>-salt of <i>O</i>,<i>O</i>′-dibenzoyl-(<i>R</i>,<i>R</i>)-tartaric acid. The absolute configuration of the 1-isopentyl-3-phospholene oxide enantiomer with negative optical rotation was also substantiated by a study involving CD spectroscopy and theoretical calculations.</p>","PeriodicalId":1,"journal":{"name":"Accounts of Chemical Research","volume":null,"pages":null},"PeriodicalIF":16.4000,"publicationDate":"2018-03-03","publicationTypes":"Journal Article","fieldsOfStudy":null,"isOpenAccess":false,"openAccessPdf":"https://sci-hub-pdf.com/10.1002/hc.21411","citationCount":"0","resultStr":"{\"title\":\"Preparation of enantiopure 1-isopentyl-3-methyl-3-phospholene 1-oxide via the formation of diastereomeric complexes\",\"authors\":\"Péter Bagi, Kinga Juhász, Mihály Kállay, Dóra Hessz, Miklós Kubinyi, Elemér Fogassy, György Keglevich\",\"doi\":\"10.1002/hc.21411\",\"DOIUrl\":null,\"url\":null,\"abstract\":\"<p>The resolution of 1-isopentyl-3-methyl-3-phospholene 1-oxide via the formation of diastereomeric complexes using TADDOL derivatives or the Ca<sup>2+</sup>-salts of tartaric acid derivatives was studied. Both enantiomers of the 1-isopentyl-3-phospholene oxide were prepared in an enantiopure form with (<i>R</i>,<i>R</i>)-spiro-TADDOL, or with the acidic Ca<sup>2+</sup>-salt of <i>O</i>,<i>O</i>′-dibenzoyl-(<i>R</i>,<i>R</i>)-tartaric acid. The absolute configuration of the 1-isopentyl-3-phospholene oxide enantiomer with negative optical rotation was also substantiated by a study involving CD spectroscopy and theoretical calculations.</p>\",\"PeriodicalId\":1,\"journal\":{\"name\":\"Accounts of Chemical Research\",\"volume\":null,\"pages\":null},\"PeriodicalIF\":16.4000,\"publicationDate\":\"2018-03-03\",\"publicationTypes\":\"Journal Article\",\"fieldsOfStudy\":null,\"isOpenAccess\":false,\"openAccessPdf\":\"https://sci-hub-pdf.com/10.1002/hc.21411\",\"citationCount\":\"0\",\"resultStr\":null,\"platform\":\"Semanticscholar\",\"paperid\":null,\"PeriodicalName\":\"Accounts of Chemical Research\",\"FirstCategoryId\":\"92\",\"ListUrlMain\":\"https://onlinelibrary.wiley.com/doi/10.1002/hc.21411\",\"RegionNum\":1,\"RegionCategory\":\"化学\",\"ArticlePicture\":[],\"TitleCN\":null,\"AbstractTextCN\":null,\"PMCID\":null,\"EPubDate\":\"\",\"PubModel\":\"\",\"JCR\":\"Q1\",\"JCRName\":\"CHEMISTRY, MULTIDISCIPLINARY\",\"Score\":null,\"Total\":0}","platform":"Semanticscholar","paperid":null,"PeriodicalName":"Accounts of Chemical Research","FirstCategoryId":"92","ListUrlMain":"https://onlinelibrary.wiley.com/doi/10.1002/hc.21411","RegionNum":1,"RegionCategory":"化学","ArticlePicture":[],"TitleCN":null,"AbstractTextCN":null,"PMCID":null,"EPubDate":"","PubModel":"","JCR":"Q1","JCRName":"CHEMISTRY, MULTIDISCIPLINARY","Score":null,"Total":0}
Preparation of enantiopure 1-isopentyl-3-methyl-3-phospholene 1-oxide via the formation of diastereomeric complexes
The resolution of 1-isopentyl-3-methyl-3-phospholene 1-oxide via the formation of diastereomeric complexes using TADDOL derivatives or the Ca2+-salts of tartaric acid derivatives was studied. Both enantiomers of the 1-isopentyl-3-phospholene oxide were prepared in an enantiopure form with (R,R)-spiro-TADDOL, or with the acidic Ca2+-salt of O,O′-dibenzoyl-(R,R)-tartaric acid. The absolute configuration of the 1-isopentyl-3-phospholene oxide enantiomer with negative optical rotation was also substantiated by a study involving CD spectroscopy and theoretical calculations.
期刊介绍：
Accounts of Chemical Research presents short, concise and critical articles offering easy-to-read overviews of basic research and applications in all areas of chemistry and biochemistry. These short reviews focus on research from the author’s own laboratory and are designed to teach the reader about a research project. In addition, Accounts of Chemical Research publishes commentaries that give an informed opinion on a current research problem. Special Issues online are devoted to a single topic of unusual activity and significance.
Accounts of Chemical Research replaces the traditional article abstract with an article "Conspectus." These entries synopsize the research affording the reader a closer look at the content and significance of an article. Through this provision of a more detailed description of the article contents, the Conspectus enhances the article's discoverability by search engines and the exposure for the research.
京公网安备 11010802042870号
京ICP备2023020795号-1
分享
求助内容：
应助结果提醒方式：
扫码关注我们
