{"title":"Synthesis of Chiral Bisoxazoline Ligands: (3a<i>R</i>,3a'<i>R</i>,8a<i>S</i>,8a'<i>S</i>)-2,2'-(cyclopropane-1,1-diyl)bis(3a,8adihydro-8<i>H</i>-indeno[1,2-<i>d</i>]oxazole).","authors":"Julie L Hofstra, Travis J DeLano, Sarah E Reisman","doi":"10.15227/orgsyn.097.0172","DOIUrl":null,"url":null,"abstract":"An oven-dried 2-L three-necked, round-bottomed flask equipped with a 6.5 cm × 2.0 cm Teflon-coated elliptical stir bar is fitted with a thermometer, a reflux condenser and a rubber septum. The system is connected to a continuous nitrogen flow and then charged with (1R,2S)-(+)-cis-1-amino-2-indanol (1, 22.2 g, 149 mmol, 2.1 equiv), diethyl malonimidate dihydrochloride (2, 16.4 g, 71 mmol, 1 equiv), and 1 L of dichloromethane (Note 2). The system is heated to 45 °C (internal temperature 43 °C) under an atmosphere of nitrogen in an oil bath for 18 h, stirring at 600 rpm. Reaction progress is monitored by 1H NMR (Note 3) (Figure 1).","PeriodicalId":520734,"journal":{"name":"Organic syntheses; an annual publication of satisfactory methods for the preparation of organic chemicals","volume":" ","pages":"172-188"},"PeriodicalIF":0.8000,"publicationDate":"2020-01-01","publicationTypes":"Journal Article","fieldsOfStudy":null,"isOpenAccess":false,"openAccessPdf":"https://www.ncbi.nlm.nih.gov/pmc/articles/PMC8294164/pdf/nihms-1625611.pdf","citationCount":"2","resultStr":null,"platform":"Semanticscholar","paperid":null,"PeriodicalName":"Organic syntheses; an annual publication of satisfactory methods for the preparation of organic chemicals","FirstCategoryId":"1085","ListUrlMain":"https://doi.org/10.15227/orgsyn.097.0172","RegionNum":0,"RegionCategory":null,"ArticlePicture":[],"TitleCN":null,"AbstractTextCN":null,"PMCID":null,"EPubDate":"2020/8/20 0:00:00","PubModel":"Epub","JCR":"","JCRName":"","Score":null,"Total":0}
引用次数: 2
Abstract
An oven-dried 2-L three-necked, round-bottomed flask equipped with a 6.5 cm × 2.0 cm Teflon-coated elliptical stir bar is fitted with a thermometer, a reflux condenser and a rubber septum. The system is connected to a continuous nitrogen flow and then charged with (1R,2S)-(+)-cis-1-amino-2-indanol (1, 22.2 g, 149 mmol, 2.1 equiv), diethyl malonimidate dihydrochloride (2, 16.4 g, 71 mmol, 1 equiv), and 1 L of dichloromethane (Note 2). The system is heated to 45 °C (internal temperature 43 °C) under an atmosphere of nitrogen in an oil bath for 18 h, stirring at 600 rpm. Reaction progress is monitored by 1H NMR (Note 3) (Figure 1).