Helena McAlonan, James P. Murphy, M. Nieuwenhuyzen, K. Reynolds, P. K. Sarma, P. Stevenson, N. Thompson
{"title":"4-苯氧恶唑烷-2- 1和异吲哚-1- 1;n -取代1,3-二烯Diels-Alder反应的手性助剂。","authors":"Helena McAlonan, James P. Murphy, M. Nieuwenhuyzen, K. Reynolds, P. K. Sarma, P. Stevenson, N. Thompson","doi":"10.1039/B108059H","DOIUrl":null,"url":null,"abstract":"Terminally N-substituted dienes derived from 3-methylisoindolin-1-one, 4-isopropyl- and 4-phenyloxazolidin-2-one undergo Diels–Alder reaction with a range of activated dienophiles. The reactions reported are completely regio- and endo-selective, with the diastereoisomeric excess with respect to the auxiliary good to excellent in most of the cases reported. A model has been developed for rationalising the stereochemical outcome of these reactions.","PeriodicalId":17267,"journal":{"name":"Journal of The Chemical Society-perkin Transactions 1","volume":"38 1","pages":"69-79"},"PeriodicalIF":0.0000,"publicationDate":"2002-12-17","publicationTypes":"Journal Article","fieldsOfStudy":null,"isOpenAccess":false,"openAccessPdf":"","citationCount":"28","resultStr":"{\"title\":\"4-Phenyloxazolidin-2-ones and isoindolin-1-ones; chiral auxiliaries for Diels-Alder reactions of N-substituted 1,3-dienes.\",\"authors\":\"Helena McAlonan, James P. Murphy, M. Nieuwenhuyzen, K. Reynolds, P. K. Sarma, P. Stevenson, N. Thompson\",\"doi\":\"10.1039/B108059H\",\"DOIUrl\":null,\"url\":null,\"abstract\":\"Terminally N-substituted dienes derived from 3-methylisoindolin-1-one, 4-isopropyl- and 4-phenyloxazolidin-2-one undergo Diels–Alder reaction with a range of activated dienophiles. The reactions reported are completely regio- and endo-selective, with the diastereoisomeric excess with respect to the auxiliary good to excellent in most of the cases reported. A model has been developed for rationalising the stereochemical outcome of these reactions.\",\"PeriodicalId\":17267,\"journal\":{\"name\":\"Journal of The Chemical Society-perkin Transactions 1\",\"volume\":\"38 1\",\"pages\":\"69-79\"},\"PeriodicalIF\":0.0000,\"publicationDate\":\"2002-12-17\",\"publicationTypes\":\"Journal Article\",\"fieldsOfStudy\":null,\"isOpenAccess\":false,\"openAccessPdf\":\"\",\"citationCount\":\"28\",\"resultStr\":null,\"platform\":\"Semanticscholar\",\"paperid\":null,\"PeriodicalName\":\"Journal of The Chemical Society-perkin Transactions 1\",\"FirstCategoryId\":\"1085\",\"ListUrlMain\":\"https://doi.org/10.1039/B108059H\",\"RegionNum\":0,\"RegionCategory\":null,\"ArticlePicture\":[],\"TitleCN\":null,\"AbstractTextCN\":null,\"PMCID\":null,\"EPubDate\":\"\",\"PubModel\":\"\",\"JCR\":\"\",\"JCRName\":\"\",\"Score\":null,\"Total\":0}","platform":"Semanticscholar","paperid":null,"PeriodicalName":"Journal of The Chemical Society-perkin Transactions 1","FirstCategoryId":"1085","ListUrlMain":"https://doi.org/10.1039/B108059H","RegionNum":0,"RegionCategory":null,"ArticlePicture":[],"TitleCN":null,"AbstractTextCN":null,"PMCID":null,"EPubDate":"","PubModel":"","JCR":"","JCRName":"","Score":null,"Total":0}
4-Phenyloxazolidin-2-ones and isoindolin-1-ones; chiral auxiliaries for Diels-Alder reactions of N-substituted 1,3-dienes.
Terminally N-substituted dienes derived from 3-methylisoindolin-1-one, 4-isopropyl- and 4-phenyloxazolidin-2-one undergo Diels–Alder reaction with a range of activated dienophiles. The reactions reported are completely regio- and endo-selective, with the diastereoisomeric excess with respect to the auxiliary good to excellent in most of the cases reported. A model has been developed for rationalising the stereochemical outcome of these reactions.