{"title":"Bifunctionalized Allenes. Part XXIII. An Efficient Method for Regioselective Synthesis of 5-Phosphorylated Allenecarboxylates","authors":"Hasan H. Hasanov, Ivaylo K. Ivanov, V. Christov","doi":"10.2478/asn-2020-0029","DOIUrl":null,"url":null,"abstract":"Abstract An efficient method for regioselective synthesis of 5-(dimethoxyphosphoryl)-allenecarboxylates by an atom economical [2,3]-sigmatropic rearrangement of the mediated 3-(dimethoxyphosphanyloxy)-alk-4-ynoates is described. Alkyl 5-(dimethoxyphosphoryl)-alka-3,4-dienoates can be readily prepared via reaction of alkyl 3-hydroxy-alk-4-ynoates with dimethylchlorophosphite in the presence of a base. Alkyl 3-hydroxy-alk-4-ynoates were prepared by reaction of the metallated acetylenes with commercialy available alkyl 3-oxoalkanoates.","PeriodicalId":7171,"journal":{"name":"Acta Scientifica Naturalis","volume":"7 1","pages":"1 - 10"},"PeriodicalIF":0.0000,"publicationDate":"2020-11-01","publicationTypes":"Journal Article","fieldsOfStudy":null,"isOpenAccess":false,"openAccessPdf":"","citationCount":"1","resultStr":null,"platform":"Semanticscholar","paperid":null,"PeriodicalName":"Acta Scientifica Naturalis","FirstCategoryId":"1085","ListUrlMain":"https://doi.org/10.2478/asn-2020-0029","RegionNum":0,"RegionCategory":null,"ArticlePicture":[],"TitleCN":null,"AbstractTextCN":null,"PMCID":null,"EPubDate":"","PubModel":"","JCR":"","JCRName":"","Score":null,"Total":0}
引用次数: 1
Abstract
Abstract An efficient method for regioselective synthesis of 5-(dimethoxyphosphoryl)-allenecarboxylates by an atom economical [2,3]-sigmatropic rearrangement of the mediated 3-(dimethoxyphosphanyloxy)-alk-4-ynoates is described. Alkyl 5-(dimethoxyphosphoryl)-alka-3,4-dienoates can be readily prepared via reaction of alkyl 3-hydroxy-alk-4-ynoates with dimethylchlorophosphite in the presence of a base. Alkyl 3-hydroxy-alk-4-ynoates were prepared by reaction of the metallated acetylenes with commercialy available alkyl 3-oxoalkanoates.
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