Sara González , Dario Del Carratore , Ricardo J. Maza , Elena Fernández
{"title":"The seriatim Cu(I) activation of 1,1,1′,1′-tetrapinacolborylethane to prospective ring closing","authors":"Sara González , Dario Del Carratore , Ricardo J. Maza , Elena Fernández","doi":"10.1016/j.tchem.2023.100045","DOIUrl":null,"url":null,"abstract":"<div><p>The synthesis and characterization of 1,1,1′1′-tetrapinacolborylethane is conducted to study the functionalization of that densely borylated small molecules through Cu-catalyzed coupling with allyl halides. A second Cu-catalyzed allylic alkylation of the homoallyl triboronate products gave access to mixed dihomoallyl diboronates. The intramolecular concatenated allylic alkylation version produced methylenecyclopentane-1,2-dipinacolboronic ester with 2:1 diastereoselection on the <em>trans</em>-diastereoisomer.</p></div>","PeriodicalId":74918,"journal":{"name":"Tetrahedron chem","volume":"8 ","pages":"Article 100045"},"PeriodicalIF":0.0000,"publicationDate":"2023-08-22","publicationTypes":"Journal Article","fieldsOfStudy":null,"isOpenAccess":false,"openAccessPdf":"","citationCount":"0","resultStr":null,"platform":"Semanticscholar","paperid":null,"PeriodicalName":"Tetrahedron chem","FirstCategoryId":"1085","ListUrlMain":"https://www.sciencedirect.com/science/article/pii/S2666951X23000116","RegionNum":0,"RegionCategory":null,"ArticlePicture":[],"TitleCN":null,"AbstractTextCN":null,"PMCID":null,"EPubDate":"","PubModel":"","JCR":"","JCRName":"","Score":null,"Total":0}
引用次数: 0
Abstract
The synthesis and characterization of 1,1,1′1′-tetrapinacolborylethane is conducted to study the functionalization of that densely borylated small molecules through Cu-catalyzed coupling with allyl halides. A second Cu-catalyzed allylic alkylation of the homoallyl triboronate products gave access to mixed dihomoallyl diboronates. The intramolecular concatenated allylic alkylation version produced methylenecyclopentane-1,2-dipinacolboronic ester with 2:1 diastereoselection on the trans-diastereoisomer.